Sail Selina, St. Michaels MD


Wine Cruises on the Selina II Sailing Yacht

Several winters ago Capt Iris took a vacation to South Africa, home to some spectacular vineyards. She’s always had an interest in wine, and now has the opportunity to share the experience of learning about and tasting wines in a fabulous setting. Available with prior reservations, these cruises include an introduction to the basics of wine tasting, sampling 3 reds and 3 whites, and scorecards for keeping track of your notes. Plus occasionally local restaurateurs and chefs drop in to share their food matching ideas (and come along for a sail, oh yea….). $85 per person, minimum 2 guests, or by private charter up to 6 guests $495. Plus there is a 10% amusement tax in St. Michaels harbor, and it is customary to tip the ship’s mate like a restaurant, 15%-20%. Wine Cruises are available 7-days a week 12:30-2:30pm and 3:00-5:00pm.

Tour Includes

  • Sampling of 3 white wines, 3 red wines, and a full glass of your favorite wine
  • Bottled Water
  • Soda & Beer also available for sale
  • Binoculars, sunscreens, sunglasses
  • Free parking, 7 days a week
  • Rain jackets, hats, blankets
  • Available 12:30-2:30 & 3:00-5:00
  •  We also offer this tour as a private charter

Why Choose Sail Selina?

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 Boats

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 to simply 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.

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