Sail Selina - St. Michaels, Maryland - Sailing Charters


Welcome to Sail Selina II,

your St. Michaels , MD authority for authentic Sailing
Charters on the Chesapeake Bay

Family Owned & Operated, Limited to just 6 guests


Best in Luxury, Best in Boat Tours, Best in Service

Looking for a boat tour or sailing charter in St. Michaels, MD? Want to get out on the water? Unique, upscale & exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sail. Come join us for a relaxing 2 hour boat ride or romantic sunset champagne cruise aboard the beautiful, authentic, and meticulously restored historic catboat Selina II.

Specializing in first class service sailboat charters, we also offer specialty outings including private charters, weddings, elopements, anniversary and birthday celebrations, girls night out, wine tasting cruises, beer tasting sails, one on one sailing lessons, and private romantic gourmet table-for-two dinner cruises.

You will be treated to an unforgettable nautical experience with third generation Captain Iris Clarke, granddaughter of the original owners. Included is a short tour of the historic St. Michaels harbor waterfront as we navigate past the Chesapeake Bay Maritime Museum's floating collection and motor by the ‘Wedding Crashers’ setting at the Inn at Perry Cabin. Then we sail out into the Miles River and follow the wind wherever it takes us on the Chesapeake Bay. Help trim the sails, or simply sit back and relax, we’re here to help complete your historic yacht charter experience.

Selina II’s 1000 square foot gaff rigged sail, highly polished bronze and freshly varnished mahogany set the tone for your adventure in sailing history. Incredibly roomy & stable, she provides the utmost in comfort and relaxation. Built in 1926, she is the largest surviving of any of the catboats built. No matter what activities or attractions in Maryland you may usually enjoy, Selina II offers the perfect boat ride to complete your perfect vacation.

We are docked at the Harbour Inn & Marina in St. Michaels, Maryland, a charming Eastern Shore town known for its wonderful seafood restaurants and quaint small town feel. We are just a short day trip from most East Coast cities including Washington DC, Baltimore, Annapolis, & Philadelphia, or stay in one of our wonderful Bed & Breakfasts and explore the town, there’s lots to do: biking, shopping, Classic Motor Museum, St Mary’s Museum, 3 world class spas,explore a lighthouse, St. Michaels winery, Eastern Shore Brewing, Lyon Distillery, golfing, kayaking, paddle boarding, boating and a host of other family attractions and activities for adults nearby.

Plus St. Michaels has a host of special events, come join us for Wine Fest in April, the Antique and Classic Boat Festival in June, view our 4th of July fireworks from the water, Watermans Appreciation Day in August, the Boat Auction in September, and the Small Craft Festival and Fall into St. Michaels in October. We hope to see you soon!

View Selina II's featured article in the
2009 Fall Bridal supplement in the Star Democrat.

"More than an experience you will never forget and will definitely return for more. Sit back, relax, and take in sights around St. Michaels. A special treat hearing about the area well as the beautiful Selina II. Each year, I look forward to a return, with over 20 sails on Selina II with Capt Iris, First Mate well as others hoisting the sails. Memorable!"

-Cyndia B, Arlington, VA, Nov 2015

101 N. Harbor Road, St Michaels MD  21663

Close to many hotels in the area including:
The Inn at Perry Cabin, Harbour Inn & Marina, Tidewater Inn, The Old Brick Inn, Dr. Dodson House

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