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Chesapeake Bay Sailing Trips in St. Michaels, MD

Sailing Tours, Sailboat Rides & Boat Trips aboard Sail Selina

Check out our most popular sailing tours in St. Michaels MD, near Annapolis! From two hour day sails with optional wine tastings and beer tastings, sunset champagne cruises, to private sailing lessons and moonlight sails, plus private charters including up to half or full-day sails, romantic elopements, and nautical weddings, we offer the best sunset cruises and a wide variety of personalized boat tours. We can also customize your St Michaels Chesapeake Bay sailing trip to create a one-of-a-kind experience!