- Most Popular
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Learn about St. Michaels Harbor while cruising along the Miles River. Sit back, relax, and enjoy the scenery!
Sailing Trips in St. Michaels
Check out our most popular sailing trips! From two hour day sails with optional wine tastings and beer tastings, sunset champagne cruises, to private sailing lessons and moonlight sails, plus private charters including up to half or full-day sails, romantic elopements, and nautical weddings, we offer a wide variety of boat tours. We can also cater your St Michaels Chesapeake Bay sailing tour to create a one-of-a-kind experience!
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- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Enjoy a breathtaking sunset while sipping a glass of Champagne and tasting delectable hors-d’oeuvres on this cruise!
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Enjoy free Champagne and chocolates while taking in the beauty of a sunset or the rising of the moon with this cruise!
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- Ages 21+ Ages Ages 21+
- Daily Availability Daily
Come aboard the Selina II and learn the basics of wine tasting and sample great vintages with Capt. Iris.
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Sit back and enjoy some great St Michaels area breweries aboard the Selina II!
- Half Day Duration Half Day
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Enjoy a small tour of St. Michaels harbor before heading out for a half-day sail up the Miles River!
- 6 People Occupancy 6 People
- Daily Availability Daily
Learn to sail with our fantastic team aboard the Selina II sailing yacht! Learn all of the basics and more.
- Full Day Duration Full Day
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Join us for a full day of sailing that includes a mini-tour of St. Michaels before cruising along the Miles River.
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Make your engagement, honeymoon, or anniversary unforgettable experience with our Romance Sail aboard the Sail Selina II.
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Take a sail aboard the Selina II with whole family and enjoy a picnic lunch!
- 2 Hours Duration 2 Hours
- 6 or More Occupancy 6 or More
- All ages Ages All ages
- Daily Availability Daily
Have an unforgettable wedding ceremony aboard Sail Selina’s yacht! You have two different wedding packages to choose from!
- 4 People Max. Occupancy 4 People Max.
- Daily Availability Daily
Join us aboard our yacht and enjoy an open bar and a three-course meal from the finest restaurants in St. Michaels.
- Multi Day Duration Multi Day
- 6 People Occupancy 6 People
- All ages Ages All ages
- Daily Availability Daily
Experience a night on the water with our overnight excursion. You also get to enjoy a picnic-style dinner and breakfast!
- 2 Hours Duration 2 Hours
- 6 People Occupancy 6 People
- Adults only Ages Adults only
- Daily Availability Daily
Getting engaged? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to propose!