• Come Sail with St. Michaels Sailing Charters!

Step aboard and experience the magic of the Chesapeake Bay with St. Michaels Sailing Charters. Whether you're seeking relaxation, romance, celebration, or adventure, our curated sailing experiences offer the perfect way to enjoy the water in beautiful St. Michaels, Maryland! Looking for a relaxing boat tour in St. Michaels on the Chesapeake Bay? Hoping to get out on the water, unwind, and spend time in nature? If you’re searching for things to do in St. Michaels, MD or exploring 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 delivers memorable, peaceful days under sail. Choose between our two stunning vessels: 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 led by 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. Choose Your Perfect Sailing Experience 2-Hour Relaxing Chesapeake Day Sail Chesapeake Bay Sunset Champagne Sail Wine Tasting Cruise Beer Tasting Cruise Nautical Wedding & Elopement Packages Half-Day Private Sail Full-Day Private Sail Private Sailing Lessons Marriage Proposal & Engagement Cruise Bachelorette & Bachelor Party Cruise Special 4th of July Fireworks Cruise Private Sailing Catamaran Charter