Bachelorette/Bachelor Party Cruise

• 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