Wine Tasting Cruise

Your Wine Tasting Experience

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.

⛵ 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

What Guests Love

• Curated Wine Selection: Six wines chosen to delight your palate.

• Relaxing Sailing Experience: Enjoy gentle breezes and Bay views while you sip.

• Stunning Scenery: Beautiful waterfront vistas of historic St. Michaels and the Chesapeake Bay.

• Friendly Crew: Knowledgeable captains and crew make every sail enjoyable and welcoming.

• Bottled Water: Always complimentary onboard.

Location

Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland, a charming Eastern Shore town celebrated for its fresh seafood, historic streets, and welcoming small-town atmosphere.

Whether you’re planning a day trip to St. Michaels or a sailing charter on the Eastern Shore of the Chesapeake Bay, our excursions are conveniently located:

• 90 minutes from Philadelphia, Baltimore, and Washington, D.C.

• 1 hour from Annapolis

Arrive early to explore the quaint town, enjoy local restaurants, or stroll along the waterfront before your relaxing sail.

Good to Know Before You Go

Arrival:
Please arrive 15 minutes prior to departure at the dock behind the Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.

Restrooms:
Lady Patty has a small marine head for emergency use, and Epiphany features a private, spacious marine head. Both are located down a short set of steps. For all guests, we recommend using the Harbour Inn lobby restrooms before boarding.

Parking:
Guests may park in the hotel lot or along the waterfront on Harbor Road past the police boats.

Shoes & Attire:
Wear comfortable shoes or something easy to remove if you prefer to go barefoot. Ladies, please avoid high heels. Light jackets or layers are recommended on cooler days.

Sunscreen & Hats:
If using spray sunscreen, please apply before boarding to protect the varnish. Don’t worry if you forget your sunhat — custom baseball caps are available for purchase onboard.

Children:
Children of all ages are welcome! Life jackets are available in infant, toddler, and youth sizes. Per U.S. Coast Guard regulations, all children count as passengers and require a ticket.

Weather:
Safety and comfort are our priority. The captain may cancel due to weather, with the final decision made about 15 minutes before departure. There is no charge if a sail is cancelled due to weather, and we will do our best to rebook you, issue a gift card, or provide a refund.

Beverages & Food:
Your cruise includes a guided tasting of six curated wines — three reds and three whites — thoughtfully selected for the experience. Additional wine by the glass and non-alcoholic beverages are available onboard for purchase. We partner with local businesses to offer pre-ordered, charter-friendly food options ready upon arrival. For full details on onboard food and beverage options, please see our policies.

Ready to Set Sail?

Raise a glass and take in sweeping Chesapeake Bay views during an unforgettable wine tasting sail. Perfect for special occasions or a relaxed outing with friends, this experience blends scenic beauty with exceptional wines.

Book your 2‑Hour Wine Tasting Sail now! Spots fill quickly, especially on weekends — reserve your seats today! 👉