2 Hour Wine Tasting Cruise on Historic 1935 Lady Patty

Your Wine Tasting Experience

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch with elegant classic lines, rich wood details, and traditional rigging that harken back to the golden age of Chesapeake sailing. This timeless yacht creates an intimate and authentic setting for a relaxed wine tasting experience on the Bay.

Guests can settle into cushioned seating along each side of the wooden cabin top or gather in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails in motion. With a small group onboard, Lady Patty offers a personal and inviting atmosphere that pairs perfectly with sipping and savoring curated wines.

Depart from the charming harbor of historic St. Michaels and enjoy a brief harbor tour, including views of the 1879 Hooper Strait Lighthouse, before gliding onto the scenic Miles River. As you sail across peaceful Chesapeake Bay waters, savor a thoughtfully selected tasting of three red and three white wines, each chosen to complement the beauty and rhythm of the experience.

Whether you’re celebrating a special occasion, planning a girls’ outing, or simply gathering with friends, this wine tasting sail blends history, scenery, and exceptional wines into a truly memorable experience on the Bay.

What Guests Love

• Curated Wine Selections: Six thoughtfully selected wines — three reds and three whites — chosen to create a rich and memorable tasting experience.

• Intimate Historic Setting: Enjoy gentle Bay breezes aboard a beautifully restored 1935 sailing ketch with classic lines and traditional charm.

• Scenic Chesapeake Views: Take in waterfront vistas of historic St. Michaels and the peaceful Miles River as you sip and sail.

• Cozy & Social Atmosphere: Cushioned seating along the cabin top and in the cockpit creates the perfect setting for relaxed conversation and wine enjoyment.

• Exceptional Crew: Friendly, knowledgeable captains who create a welcoming experience

Location

Lady Patty is 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, located down a short set of steps. Guests are encouraged to use 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?

Experience the beauty of the Chesapeake Bay aboard a historic ketch while savoring a curated wine tasting. Whether you’re planning a romantic outing, a girls’ night, or a relaxing escape with friends, your memorable time on the water awaits.

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