Learn about St. Michaels Harbor while cruising in a historic sailing yacht along the Miles River. Sit back, relax, and enjoy the scenery!
Sail Selina II
Chesapeake Bay Sailing Tours, Sailboat Rides & Boat Trips in St. Michaels, MDClick here to View All Sailing Charters
Our Popular Sailing Charters
Best in Luxury, Best in Boat Tours, Best in Service
Looking for a Chesapeake Bay boat tour, sailboat rides or sailing charter in St. Michaels, MD? Want to get out on the water? Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just six guests for an intimate taste of the history of sailing.
Come join us for a relaxing two-hour sailing trip, or your St Michaels sail boat ride could be a romantic sunset champagne cruise aboard the beautiful, authentic, and meticulously restored historic catboat Selina II.
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! Sail Selina II is ranked the #1 boat tour in St. Michaels and has been for 15 years running.
Everything Is Included
Sit back and relax. Want a drink? We’ve got it! Beer, wine, Champagne, and soda are available for sale on all our sailboat rides and are included on our evening charters.
Over 92 Years of Experience
Sail Selina’s skippers have a combined sailing history of 90+ years, and her 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
And all that is in a gorgeous setting. Sail Selina was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. A perfect setting for the ultimate charter boat in St Michaels. Join us for a sailing charter boat tour 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 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.