Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized boat tour!
Our Popular St Michaels Maryland Sailing Charters and Relaxing Sailboat Cruises
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.
Best Relaxing Luxury Sail Boat Tours in Chesapeake Bay
Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sailing.
With freshly varnished mahogany, brightly polished brass, and comfortable seating let Sail Selina II, the premier sailboat in St Michaels, MD be your sightseeing charter boat. Hop aboard Sail Selina II and experience another time and place.
Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting cruises, beer tasting cruises, moonlight sails and more.
For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.
If you are looking for things to do in St Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.
Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.
Looking to relax? We are the St Michaels boat ride to choose!
Learn more about the history of our sailboat and all the fun things to do in St Michaels, MD here:
The #1 Boat Tour in St. Michaels on TripAdvisor!
Why Sail Selina II?
Rated #1 on TripAdvisor
When looking for things to do in St Michaels MD, our reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.
Everything Is Included
Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.
Over 92 Years of Experience
Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!
Spacious & Beautiful Boat
All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.
The Best Captains
Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.