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


Book your Sailing Tours & Sunset Champagne Cruises or Learn to Sail with SAIL SELINA II

Chesapeake Bay Sailing Charters

Tour St. Michaels waterfront before heading out of the harbor as we put up sails and follow the wind.

2 hour Chesapeake Day Sail

Sunset Champagne Cruise

Moonlight Cruise

Private Charters

Sailing Lessons

Romance Packages

Family Vacations

Wine Tasting Cruises

Beer Tasting Cruises

Nautical Weddings

Overnight Excursions

Dinner Sails

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!

Why Choose Sail Selina?

When we ask guests why they had such a great time on their trip with Sail Selina, we hear responses like ‘Your tour exceeded our expectations’ and ‘You guys gave a great tour, knowledgeable, engaging, and yet totally relaxing’. Whether you participate raising sails or simply sit back and relax, our crew is proud to share our enthusiasm for the the Eastern Shore of Chesapeake Bay, our love for sailing, and our heartfelt passion for the beautiful historic yacht Selina II. We hope you’ll come join us for that experience and enjoy a nostalgic taste of the history of sail.

Rated #1 in TripAdvisor

Reviews tell the story; Sail Selina is ranked the #1 Boat Tour in St Michaels and has been for 15 years running. Folks who have sailed with us often tell us their cruise with us was the highlight of their vacation. Plus, we are proud of all our other great 5 star ratings on sites like Yelp, Google, Facebook and Wedding Wire.

Everything is included

Sit back and relax. Want a drink? we’ve got it! Beer, Wine, Champagne and soda is available for sale on all trips and is included on our evening sails. Bottled Water is complimentary. Binoculars, blankets, and should you forget them hats, sunglasses, sunscreen, etc are available for our guests.

92+ Years Experience

Sail Selina has been offering sailboat rides to guests in the Chesapeake Bay area for over 15 years, her skippers have a combined sailing history of 90+ years, her crew another combined sailing history of 30+ years. We all love to sail !!

Spacious/Beautiful Boat

Cat Boats are known for their roominess. At 41′ long and 16′ wide, we have gracious uncovered seating in the cockpit with four captains chairs and 2 double settees. Even the tallest guests have plenty of room to stretch out. And all that 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. Many people tell us the photos dont due justice to how beautiful the wood workmanship is.

Best Captains

Our Captains are known for their story telling skills and offer a trip balanced with some touring, some sailing, and some opportunity tosimply relax and kick back. They share a passion for sailing, have a deep understanding of the area’s history, ecology & environmental issues, and have a great affection for our vessel Sail Selina.

Book your Next Trip With Sail Selina

Ready to book your next Sailing Charter, Fishing Trip, Corporate event, Sailing Lesson or Bachelorette Party?

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