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Chesapeake Bay Sailing Trips in St. Michaels, MD

Sailing Tours, Sailboat Rides & Boat Trips aboard Sail Selina

Discover your perfect sailing adventure in St. Michaels MD, just a leisurely 1-hour drive from Annapolis! Whether you’re dreaming of a serene 2 hour Chesapeake Day Sail, complete with optional wine and beer tastings, or imagining of the romance of a sunset champagne cruise, we have the ideal experience waiting for you.

Picture yourself learning the ropes with Private Sailing Lessons or dancing under the stars on a magical Moonlight Cruise. Looking for something truly special? Our private charters offer flexibility, with options for half or full-day sails, romantic elopements, and enchanting nautical weddings.

At, we’re dedicated to crafting unforgettable moments on the water. Our personalized boat tours cater to your every desire, ensuring your experience is nothing short of extraordinary. Plus, we’re experts in customization! Let us tailor your St Michaels Chesapeake Bay sailing trip to create a one-of-a-kind adventure just for you.

Get ready to set sail and create memories that will last a lifetime. Book your dream sailing tour with us today.