St. Michaels Sailing Charters

Looking for a relaxing boat tour in Saint Michaels on the Chesapeake Bay? Hoping to get out on the water, unwind, and spend some time in nature? If you're searching for things to do in St. Michaels, MD or exploring the top local attractions, our luxury sailing yachts—Lady Patty and Epiphany—are the perfect choice. From historic charm to modern comfort, St. Michaels Sailing Charters will take you out for a memorable and peaceful day under sail. 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.