Local Event

Wine Tasting Cruise On Historic Lady Patty!

Cost: $115-$1195

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.

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.

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.

Tags

• event
• sailing
• boat charter
• red wine
• white wine
• st. michaels
• Things to do in St. Michaels, Maryland
• Maryland Wine & Food Events
• St. Michaels Wine & Food Events