2 Hour Relaxing Chesapeake Day Sail on Lady Patty

Your Sailing 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 offers an intimate, authentic experience for a small group, letting you 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 in the rear cockpit beside the captain — a favorite spot for conversation and watching the sails in action. Whether you want 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.

Set sail from the charming harbor of historic St. Michaels and enjoy a brief harbor tour, including views of the 1879 Hooper Strait Lighthouse, before gliding out onto the scenic Miles River. Take in sweeping Chesapeake Bay vistas, peaceful waters, and the chance to spot local wildlife such as osprey, eagles, and occasionally dolphins.

Whether you prefer a quiet, relaxing ride or want to help as part of the crew, our friendly captains and experienced team ensure your sail is enjoyable, safe, and unforgettable.

What Guests Love

• Beautiful, Well‑Maintained Boats: Comfortable seating and clean vessels make for a great sailing experience.

• Friendly & Knowledgeable Crew: Captains share stories, local history, and sailing insight.

• Relaxing Escape: Perfect for families, couples, or solo travelers looking to unwind.

• Beverages & Tasting Options:Beer and wine tastings are available for an additional fee; bottled water is complimentary. Soft drinks and champagne are also available for purchase.

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:
Beer and wine tastings are available for an additional fee, along with optional sodas and champagne for purchase. Bottled water is complimentary. 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 from the deck of a historic sailing yacht. Whether you’re planning a romantic outing, family adventure, or relaxing escape with friends, your time on the water awaits.

Book your 2‑Hour Chesapeake Day Sail now! Spots fill quickly, especially on weekends and sunset sails — reserve your seats today! 👉