Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 44-foot Leopard catamaran. Each sail includes a two-hour (or longer) cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience. Enjoy our popular day sails or opt for specialty outings like sailing lessons, wine and beer tasting cruises, and more.
Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.
Out on the open water, our sailboats offer your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. Your charter begins with a peaceful glide through the harbor before heading out into the Miles River, where you’ll enjoy sweeping views and, if you’re lucky, wildlife sightings like osprey and bald eagles. This year, we’ve even spotted porpoises!
Read more about each of our yachts below:
Lady Patty carries a rich maritime legacy dating back to 1935 when she was built in Solomons Island, Maryland. Originally designed as an offshore racing yacht, she was later restored as a charter sailboat while retaining her original wooden cockpit, wheel, and mast.
This historic yacht accommodates up to 13 passengers and is maintained for both safety and comfort, offering modern-day sailors a unique chance to experience the Chesapeake Bay aboard a true piece of maritime history.
In her early years, Lady Patty raced along the Southern Ocean Racing Conference circuit in Florida, including a notable victory from St. Petersburg to Havana. Her original owner even sailed her through the Panama Canal to San Francisco to compete in the Transpac, a two-week race from California to Hawaii.
Epiphany, our 44-foot Leopard catamaran, is the ideal setting for a relaxing day on the water with up to 13 of your family members and friends. Designed for comfort, she features both forward and aft cockpit areas covered by a continuous hardtop, offering excellent protection from the elements. The aft cockpit’s spacious dining table is the perfect spot to enjoy a charcuterie board along with a selection of wine, beer, and soft drinks available for purchase. Up front, the trampoline area offers a relaxing place to sunbathe or simply soak in the sweeping Chesapeake Bay views as we sail.
Families are always welcome—kids of all ages can join in the fun. For added peace of mind, we’ve installed safety netting around the entire perimeter of the boat and provide life jackets in all sizes. Epiphany is the perfect setting for a family reunion, anniversary celebration, or any special gathering on the water!
Epiphany is also an unforgettable setting for a proposal, elopement, or intimate wedding celebration.
Here are images of both of our vessels, along with links below to book your charter with us today!
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