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Sailing Trips in St. Michaels

Check out our most popular sailing trips! 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 a wide variety of boat tours. We can also cater your St Michaels Chesapeake Bay sailing tour to create a one-of-a-kind experience!