Chesapeake Bay Sailing Trips in St. Michaels, MD

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake Bay 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 with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Step aboard the Sail Selina II and begin your journey with an enchanting tour of historic St. Michaels harbor, where every dock and waterway whispers tales of maritime lore. As the sails catch the breeze, feel the excitement of setting off on a 4-hour half-day sail up the stunning Miles River. The landscape unfolds with panoramic views of Chesapeake Bay, where shimmering waters meet lush shorelines.

This isn’t just a boat tour—it’s an unforgettable journey through time and tide, where history and nature come alive. Book now to secure your spot on this exclusive Chesapeake Bay adventure, and create memories that will last a lifetime.

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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.

Join us on May 3, 2025, for an unforgettable evening, a 1902s gala as we celebrate 25 years. Whether you don your best period attire or dress in modern elegance, come prepared to dance, dine, and toast to a quarter-century of history on the Chesapeake Bay.

Take a boat tour aboard St Michaels Sail Selina II with whole family and introduce the kids to the history of sail!

Want a wedding on a boat? Exchange your vows aboard the historic Sail Selina, surrounded by the sparkling waters of Chesapeake Bay and the gentle sway of a vintage sailboat. Choose from enchanting options: a Ceremony Under Sail or a Wharf-Side Wedding. Let the wind and waves create an unforgettable nautical backdrop❤️

❤️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!