Sailing Trips | Sail Selina II

Hop Aboard the Selina II

Check out our most popular sailing trips! From two hour day sails with optional wine and beer tastings to sailing lessons and moonlight cruises, plus private charters including up to half or full-day sails, we offer a wide variety of sailing trips. We can also cater your sailing trip to create a one-of-a-kind experience!

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Most Popular

From $85

2 Hours
6 People
All ages
Daily

Sunset Champagne Cruise

Enjoy a breathtaking sunset while sipping a glass of Champagne and tasting delectable hors-d’oeuvres on this cruise!

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From $65

2 Hours
6 People
All ages
Daily

Two Hour Chesapeake Day Sail

Learn about St. Michaels Harbor while cruising along the Miles River. You can join us as a crew member or sit back, relax, and enjoy the scenery!

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From $85

2 Hours
6 People
All ages
Daily

Moonlight Cruise

Enjoy free Champagne and chocolates while taking in the beauty of a sunset or the rising of the moon with this cruise!

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From $995

8 Hours
6 People
All ages
Daily

Full-Day Private Sail

Join us for a full day of sailing that includes a mini-tour of St. Michaels before cruising along the Miles River.

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From $665

4 Hours
6 People
All ages
Daily

Half-Day Private Sail

Enjoy a small tour of St. Michaels harbor before heading out for a half-day sail up the Miles River!

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From $365

6 People
Daily

Private Sailing Lessons

Learn to sail with our fantastic team aboard the Selina II sailing yacht! Learn all of the basics and more.

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2 Hours
6 People
All ages
Daily

Romance Packages

Make your engagement, honeymoon, or anniversary unforgettable experience with our Romance Sail aboard the Sail Selina II.

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2 or 4.5 Hours
6 People
All ages
Daily

Family Vacation Packages

Take a sail aboard the Selina II with whole family and enjoy a picnic lunch!

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From $85

2 Hours
6 People
Ages 21+
Daily

Wine Tasting Cruises

Come aboard the Selina II and learn the basics of wine tasting and sample great vintages with Capt. Iris.

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From $85

2 Hours
6 People
All ages
Daily

Beer Tasting Cruises

Sit back and enjoy some great St Michaels area breweries aboard the Selina II!

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From $650

2 Hours
6 or More
All ages
Daily

Nautical Wedding Package

Have an unforgettable wedding ceremony aboard Sail Selina’s yacht! You have two different wedding packages to choose from!

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From $2145

18 Hours
6 People
All ages
Daily

Overnight Excursions

Experience a night on the water with our overnight excursion. You also get to enjoy a picnic-style dinner and breakfast!

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4 People Max.
Daily

Private Dinner Sail

Join us aboard our yacht and enjoy an open bar and a three-course meal from the finest restaurants in St. Michaels.

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Sailing Trips in St. Michaels

Hop Aboard the Selina II