Half-Day Private Sails

• 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