Wine Tasting Cruise

Discover a truly unforgettable wine tasting cruise on the Chesapeake Bay. After boarding, you’ll set sail from historic St. Michaels and enjoy the gentle Bay breezes as you glide out onto the water.

During this 2-hour voyage, savor the rich aromas and flavors of three red and three white wines, thoughtfully selected from around the world. Our curated wine list changes regularly, offering a fresh and personalized tasting journey each time.

Whether you’re celebrating a special occasion, planning a girls’ night out, or simply enjoying time with loved ones, this wine cruise is a delicious way to experience the beauty of St. Michaels from the water. Sip, relax, and take in stunning views while our friendly, experienced crew ensures your comfort and enjoyment.

 

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.

• Per-person: $115

• Up to 13 Guests

• Private Charters Available

• 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

• Per-person: $195

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

• Private charters available

• Note: Tax and gratuity are added at checkout