Lady Patty – A Historic Chesapeake Bay Sailing Yacht
Step aboard Lady Patty, a beautifully restored 1935 wooden ketch, and experience sailing on the Chesapeake Bay the way it was meant to be. Departing from St. Michaels, Maryland, Lady Patty offers private sailing charters aboard a vessel that carries nearly a century of maritime history.
With her classic wooden construction, tall masts, and traditional rigging, Lady Patty delivers a sailing experience that feels timeless. Whether you’re looking for a relaxing cruise on the Miles River, a sunset sail, or a private charter with friends and family, sailing aboard Lady Patty is both a journey across the water and a step back into Chesapeake sailing tradition.
The Story of Lady Patty
Lady Patty was built in 1935 in Solomons Island, Maryland, during the golden age of wooden yacht construction on the Chesapeake Bay. Designed as an offshore racing yacht, she quickly proved herself as a capable and competitive vessel.
In her early years, Lady Patty raced along the East Coast and competed in major offshore sailing events. One of her notable achievements was winning the demanding St. Petersburg to Havana Race, a prestigious offshore race that challenged sailors with long passages and open ocean conditions.
Over time, Lady Patty transitioned from a racing yacht into a beloved cruising vessel. Like many historic wooden boats, she has been carefully maintained and restored throughout her life, preserving the craftsmanship and character that make classic yachts so special.
For many years, Lady Patty sailed the waters of the Chesapeake Bay out of Tilghman, Maryland, becoming a familiar and beloved sight in the region. Eventually she was sold and moved north to Nantucket, where she continued her sailing life far from the waters she was built to sail.
Today, St. Michaels Sailing Charters is proud to bring Lady Patty home to Maryland, returning this classic sailing vessel to the Chesapeake Bay. After years away, she once again sails the waters where her story began.
Today, guests who step aboard Lady Patty are not simply taking a sailing tour — they are sailing on a living piece of Chesapeake maritime history.
Why Sail on Lady Patty
There are many ways to explore the Chesapeake Bay, but sailing aboard Lady Patty offers a truly unique experience.
A Piece of History
Few charter vessels can match Lady Patty’s over 90 years of sailing history. Every plank, mast, and line reflects generations of craftsmanship and adventure.
Classic Wooden Yacht
Lady Patty is a traditional wooden sailing vessel, offering the beauty, warmth, and character that modern fiberglass boats simply cannot replicate.
Authentic Sailing Experience
Guests experience real sailing — the quiet movement of wind in the sails, the sound of water along the hull, and the peaceful rhythm of the Chesapeake Bay.
Small and Intimate Charters
With space for up to 13 guests, Lady Patty provides a relaxed and personal sailing experience perfect for families, couples, and small groups.
The Perfect Setting
Departing from the harbor of St. Michaels, one of the Chesapeake Bay’s most charming waterfront towns, Lady Patty sails the scenic waters of the Miles River, a tributary of the Chesapeake Bay.
Lady Patty Specifications
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Year Built: 1935
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Place Built: Solomons Island, Maryland
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Type: Classic Wooden Ketch
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Rig: Two-masted sailing rig
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Passenger Capacity: Up to 13 guests
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Home Port: St. Michaels, Maryland
Many original design elements remain part of Lady Patty today, including her traditional cockpit layout and classic sailing rig.
Sailing Charters Aboard Lady Patty
Lady Patty offers a variety of sailing experiences designed to showcase the beauty of the Chesapeake Bay.
Daytime Sailing Cruises – Enjoy a relaxing cruise on the Miles River, a tributary of the Chesapeake Bay, while taking in the scenery, wildlife, and classic waterfront views of St. Michaels.
Sunset Sailing – One of the most popular experiences aboard Lady Patty. Watch the sun sink over the Chesapeake Bay as the sky fills with color and the water turns golden.
Private Charters – Perfect for birthdays, family gatherings, celebrations, or simply a special day on the water with friends.
Custom Sailing Experiences – The crew can tailor a sailing experience that fits your group, whether you’re looking for a peaceful cruise or a more hands-on sailing adventure.
What to Expect on Your Sail
A typical sailing charter aboard Lady Patty is relaxed, scenic, and unforgettable.
Guests are welcome to sit back and enjoy the ride, or, if they wish, learn more about sailing and the workings of a classic wooden yacht. As the wind fills the sails, the boat glides quietly across the water, offering stunning views of the Chesapeake Bay and its wildlife.
Bring your camera — the light, water, and historic beauty of Lady Patty make every sail memorable.
Frequently Asked Questions
How many passengers can Lady Patty accommodate?
Lady Patty can carry up to 13 passengers.
Do we need sailing experience?
Not at all. Guests are welcome to simply relax and enjoy the sail.
Can we bring food and drinks?
Yes. Many guests bring snacks, wine, or a picnic to enjoy during their cruise.
What happens if the weather is bad?
Safety always comes first. If weather conditions are unsafe, charters can be rescheduled.
Book Your Sailing Adventure
There is no better way to experience the Chesapeake Bay than aboard a classic wooden sailing yacht.
Join us aboard Lady Patty and discover the beauty, history, and tradition of Chesapeake sailing.
Book your St. Michaels sailing charter today and step aboard a vessel that has been sailing for nearly a century.
