• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

Located in the heart of St. Michaels

Dine in (air conditioned dining room), on our patio or take out!

 

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

 

Get ready to spice up your Tuesdays with our unbeatable Taco Tuesday special!
Enjoy 3 of our mouth-watering Pancho Villa Tacos for just $10!

These tacos are packed with authentic flavors that will transport your taste buds straight to Mexico.

And don’t forget to pair them with our refreshing House Margaritas, available every day for only $6! 

Bring your friends, bring your family, and make San Miguels your go-to spot for Taco Tuesday. 

Located in the heart of St. Michaels

Dine in (air conditioned dining room), on our patio or take out!

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

When you get 15% off your meal!

Come and enjoy breakfast or lunch on our wrap around deck, enclosed patio or indoor dining rooms while you save 15% OFF you meal! Choose from our favorite menu items...Crab Melt, Shrimp Salad, Bacon Avocado Burger, Chicken Pot Pies and so much more!
Call NOW! 410-200-8572
*60 years or older
 

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

 

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

 

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

Located in the heart of St. Michaels

Dine in (air conditioned dining room), on our patio or take out!

 

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

 

Get ready to spice up your Tuesdays with our unbeatable Taco Tuesday special!
Enjoy 3 of our mouth-watering Pancho Villa Tacos for just $10!

These tacos are packed with authentic flavors that will transport your taste buds straight to Mexico.

And don’t forget to pair them with our refreshing House Margaritas, available every day for only $6! 

Bring your friends, bring your family, and make San Miguels your go-to spot for Taco Tuesday. 

Located in the heart of St. Michaels

Dine in (air conditioned dining room), on our patio or take out!

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

When you get 15% off your meal!

Come and enjoy breakfast or lunch on our wrap around deck, enclosed patio or indoor dining rooms while you save 15% OFF you meal! Choose from our favorite menu items...Crab Melt, Shrimp Salad, Bacon Avocado Burger, Chicken Pot Pies and so much more!
Call NOW! 410-200-8572
*60 years or older
 

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

 

• Duration: 7 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your full day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Full Day Private Charter: $2,795

• Up to 13 Guests

• 7 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Full Day Private Charter: $2,495

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 7 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 4.5 Hours
• Ages: All ages
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Set sail from the charming harbor of historic St. Michaels and enjoy a harbor cruise, including views of the 1879 Hooper Strait Lighthouse. Then venture onto the scenic Miles River and Chesapeake Bay, taking in expansive waterfront vistas, gentle breezes, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you want a relaxing, leisurely sail or prefer to join in and help with sailing duties, our friendly captains and experienced crew make your half-day on the water safe, engaging, and truly unforgettable.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• Half Day Private Charter: $1,895

• Up to 13 Guests

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• Half Day Private Charter: $1,695

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• 4 1/2 Hours

• Note: Tax and gratuity are added at checkout

• Duration: 2 Hours
• Occupancy: Up to 13 People
• Ages: All ages
• Availability: Daily
• Vessel: Clean & Safe
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany
• Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings
• #1: #1 Boat Tour in St Michaels
• Google Reviews: Over 1,200 5 star reviews!

Ready to get engaged? Create a moment you’ll never forget with a proposal aboard a sailing yacht. This thoughtfully designed Engagement Package offers a truly meaningful and unforgettable way to pop the question on the water.

Experience the perfect blend of luxury and personalized service with St. Michaels Sailing Charters. Our beautiful sailboats provide an intimate setting for couples looking to celebrate life’s most special moments. Fall in love all over again while sailing the Chesapeake Bay, surrounded by breathtaking views and timeless romance.
 

After the proposal, toast to your new chapter with a celebratory bottle of champagne—because a little bubbly always makes a meaningful moment even sweeter.

Our two-hour marriage proposal package includes a fully captained private yacht charter, a scenic harbor tour, the raising of the sails, and a relaxing sail along the Miles River. Congratulations on your nautical engagement!

• Duration: 2 Hours
• Ages: Ages 21+
• Availability: Daily
• Occupancy: 13 Guests on Lady Patty, 6 Guests on Epiphany (Epiphany is also available for private bareboat charters for up to 13 guests)
• Check-in: 15 minutes prior to departure
• Location: Harbour Inn, 101 N Harbor Road, St Michaels MD
• Free Cancellation: 72 hours before departure for private charters
• Reviews: TripAdvisor's #1 Boat Tour in St Michaels

Kick off your celebration with a festive and relaxed cruise across the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the refreshing Bay breeze and scenic water views as you mingle with your group.

Throughout your 2-hour cruise, all wine, beer, champagne, and non-alcoholic drinks are included — thoughtfully poured to keep the good times flowing. Whether you’re toasting an engagement, counting down to the big day, or just enjoying time with friends, this cruise combines great drinks with unforgettable scenery.

Sip and celebrate as you take in beautiful waterfront vistas, historic harbor views, and the peace of open water. Our friendly, experienced crew keeps the festive vibe going while ensuring your comfort and safety from start to finish.

Choose Your Vessel

? Lady Patty – Historic Sailing Ketch

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that reflect the golden age of Chesapeake sailing. This timeless yacht offers an intimate, authentic experience for a small group, allowing you to truly connect with the wind, water, and rhythm of the Bay.

Guests can relax on cushioned seating along each side of the wooden cabin top or enjoy comfortable seating in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails at work. Whether you prefer to sit back and take in the scenery or participate in light sailing duties, Lady Patty provides a hands-on, memorable experience that feels both personal and historic.

• 2 Hour Private Charter: $995

• Up to 13 Guests

• Note: Tax and gratuity are added at checkout

? Epiphany – Modern Catamaran

Experience sailing aboard Epiphany, a spacious and stable modern catamaran designed for comfort, entertainment, and panoramic views. Built with charter guests in mind, her wide beam provides exceptional stability and room to move about with ease. The captain operates from a dedicated helm station, allowing the mate to focus on enhancing your onboard experience and hospitality.

Epiphany offers abundant cushioned seating throughout shaded front and rear cockpit areas, complete with two dining tables for drinks and food. Guests can choose from bow pulpit seats, reclining captain’s chairs, built-in cushioned cockpit seating with pillows, inside salon seating, and multiple counters and tables. For a front-row view of the sail, lounge on comfy beanbag chairs at the bow or stretch out on the trampoline and watch the water glide beneath you. With modern kitchen amenities and thoughtful touches throughout, Epiphany is ideal for families, groups, or anyone seeking a relaxed, scenic, and luxurious cruise on the Chesapeake Bay

• 2 Hour Private Charter: $895

• Up to 6 Guests (Epiphany is also available for private bareboat charters for up to 13 guests)

• Note: Tax and gratuity are added at checkout