Gift Certificates - The gift of adventure!
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. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy the outdoor scenery on your personalized boat tour!
Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.
Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY 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.
Looking for a fun and refreshing way to quench your thirst while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!
Enjoy a knowledgeable and engaging tour of historic St. Michaels harbor before heading out for a 4 hour half-day sail boat tour up the beautiful Miles River on Chesapeake Bay.
Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.
Join us for a full day of sailing (8 hrs) on this boat tour that includes a mini-tour of the St. Michaels harbor before cruising along the Miles River and discovering its hidden coves enjoying the views and wildlife of Chesapeake Bay.
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 pop the question!
