2 Hour Relaxing Day Sail on Lady Patty
St. Michaels Sailing Charters
Ready to embark on an unforgettable adventure? Enjoy a two-hour cruise on historic 1935 ketch Lady Patty with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience.
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. Several years, we have even spotted dolphins!
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.
You are welcome to participate as a working crew member or simply sit back and relax; we’re here to help you complete your Chesapeake Bay sailing experience!
Beer/wine tasting is available as an add-on for 21 and older guests. The beer tasting is an unlimited sampling of 6 Maryland craft beers, the wine tasting is a flight of 3 wines.
