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: Lady Patty, a historic 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, sunset sails, wine and beer tasting cruises, private charters, or learn to sail through our American Sailing Association (ASA) certification courses, including ASA 104 Bareboat Cruising and ASA 114 Cruising Catamaran.
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, booking a sailing charter on the Chesapeake Bay, or earning your ASA sailing certification, our relaxing sailboat excursions and sailing school are conveniently located just 90 minutes from Baltimore and Washington, D.C., about an hour from Annapolis, and within easy driving distance of Philadelphia.
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, bald eagles, and even the occasional porpoise.
Learn more about the history of our sailboats and all the fun outdoor activities in St. Michaels, MD here: