Special Rum Tasting Sail on Historic 1935 Lady Patty

Your Rum Tasting Experience

Enjoy a guided rum tasting from LYON RUM, Maryland’s oldest distillery, aboard Lady Patty! A true cane-to-glass rum experience, led by founder Jaime Windon, the tasting is designed to be educational and entertaining: learn about the global history and American roots of this diverse cane spirit, as well as how it is produced, and why rum is our favorite spirit. LYON RUM includes an expansive portfolio of award-winning rums and rum liqueurs; all fermented, distilled, barreled, infused and bottled, just steps from the Lady Patty and the Chesapeake Bay, since 2013.

This small-group experience accommodates up to 12 guests, providing plenty of opportunities to interact with Jaime, ask questions, and enjoy a personalized tasting experience. To make the experience even more memorable, each guest receives a commemorative Lady Patty tasting glass featuring our exclusive logo to take home.

Lady Patty is 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 a variety of rum.

What Guests Love

• Guided by the Founder: Taste and learn directly from LYON RUM founder Jaime Windon.
• Award-Winning Local Rum: Sample handcrafted rums and liqueurs made in St. Michaels.
• Take Home a Keepsake: Your tasting includes a commemorative Lady Patty logo tasting glass to keep as a souvenir.
• Historic Sailing Experience: Cruise aboard the beautifully restored 1935 sailing ketch Lady Patty.
• Small-Group Setting: Limited to 12 guests for a personal and interactive experience.
• Scenic Chesapeake Views: Enjoy Bay breezes and beautiful waterfront scenery while you sip and sail.
• A True St. Michaels Experience: Local rum, local history, and unforgettable sailing combined.

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 local LYON RUM thoughtfully selected for the experience. Wine/beer 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 rum 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 Rum Tasting Sail now! Spots fill quickly, especially on weekends — reserve your seats today! 👉