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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!
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Learn about St. Michaels Harbor while cruising in a historic sailing yacht along the Miles River on the Eastern Shore of Chesapeake Bay. Sit back, relax, and enjoy the outdoor scenery on your personalized boat tour!
Enjoy a breathtaking Chesapeake Bay sunset while sipping a glass of Champagne or handcrafted beer or wine on this romantic St Michaels, MD sunset cruise near me!
Enjoy free Champagne while taking in the beauty of a sunset or the rising of the moon aboard this romantic Moonlight Cruise!
Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion. Our wine cruise is just an hour from Annapolis, making it the perfect day trip.
Sit back and enjoy some great St Michaels area breweries aboard the Selina II!
Enjoy a small tour of St. Michaels harbor before heading out for a half-day sail up the Miles River!
Learn to sail with our fantastic team aboard the Selina II sailing yacht! Learn all of the basics and more.
Join us for a full day of sailing that includes a mini-tour of St. Michaels before cruising along the Miles River.
Make your engagement, honeymoon, or anniversary unforgettable experience with our Romance Sail aboard the Sail Selina II.
Take a boat tour aboard St Michaels Sail Selina II with whole family and introduce the kids to the history of sail!
Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from: boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.
Getting engaged? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to propose!
Join us for dinner on a boat aboard our St Michaels Maryland sailing yacht and enjoy an open bar and a three-course meal from the finest restaurants in St. Michaels. Whether its a private yacht dinner for two or a party of 4 we can accommodate your dining needs in a spectacular setting.
Experience a night on the water with our overnight excursion. You also get to enjoy a picnic-style dinner and breakfast!
