Beer Tasting Cruises on Historic 1935 Lady Patty

Your Beer Tasting Experience

Step aboard Lady Patty, a beautifully restored 1935 sailing ketch that captures the timeless spirit of Chesapeake sailing. With her classic lines, warm wood details, and traditional rigging, she offers an intimate and authentic setting for a relaxed craft beer tasting on the water.

Guests can settle into cushioned seating along the cabin top or relax in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails in action. With the gentle heel of the boat and the steady rhythm of the wind, Lady Patty creates a hands-on, immersive experience that feels both historic and personal. Whether you prefer to simply unwind or take part in light sailing, every moment feels connected to the Bay.

Depart from the charming harbor of historic St. Michaels and enjoy a brief harbor cruise, including views of the 1879 Hooper Strait Lighthouse, before gliding onto the scenic Miles River. As you sail across peaceful Chesapeake waters, savor a curated selection of six craft beers showcasing a range of styles and flavor profiles, thoughtfully chosen to create a memorable tasting experience.

This cruise pairs exceptional craft beer with classic sailing charm and stunning waterfront scenery — perfect for celebrations, casual gatherings with friends, date nights, or anyone looking to enjoy a uniquely refreshing experience aboard a true Chesapeake icon.

What Guests Love

• Curated Beer Selections: Six craft beers chosen to showcase a variety of styles and flavors.

• 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 craft beers, thoughtfully selected to showcase a range of styles and flavors. Wine and non-alcoholic beverages are available for purchase onboard. 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 aboard Lady Patty and enjoy sweeping Chesapeake Bay views on an unforgettable beer tasting sail. Ideal for special occasions or a laid-back outing with friends, this experience pairs scenic beauty with exceptional craft beer for a truly refreshing time on the water.

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