Sailing Charters in St. Thomas & St. John
Wind in the sails, the islands at your pace. Our sailing fleet runs the classic Virgin Islands route — sunset cruises off St. Thomas, full-day sails to St. John's north shore, and longer passages to the BVI for sailors who want the real thing.
We’ve selected the best Boats for you
charters available
Sea Level — 50′ Ketch-Rigged Monohull
Toast the evening aboard Sea Level, a classic 50′ ketch-rigged sailing yacht, on a 2.5-hour private sunset sail from Compass Point Marina. Relax on cushioned deck seating with chilled sparkling wine, South Carolina–style peel-and-eat shrimp, and a premium open bar as the Caribbean sky lights up. Pedro the sailing dog may join you.
- Sparkling wine at golden hour
- Peel-and-eat shrimp & hors d'oeuvres
Sea Level — 50′ Ketch-Rigged Monohull
Set sail on a relaxed 3.5-hour afternoon aboard Sea Level, a classic 50′ ketch-rigged sailing yacht. Cruise the turquoise waters around St. Thomas, snorkel crystal-clear reefs, and float on the water oasis — with the option to pull up to Pizza Pi at Christmas Cove. Hors d'oeuvres, an open bar, and Pedro the pirate dog round out the day.
- Relaxed 3.5-hour afternoon sail
- Snorkel reefs & stop at Pizza Pi
Sea Level — 50′ Ketch-Rigged Monohull
Sail the U.S. Virgin Islands aboard Sea Level, a classic 50′ ketch-rigged sailing yacht and the flagship of Happy Island Charters. Spend the day snorkeling reefs, swimming secluded coves, and floating on the water oasis, then sit down to their famous gourmet Lowcountry Boil with Caribbean lobster. You might even sail with Pedro, the resident pirate dog.
- Gourmet Lowcountry Boil with Lobster
- Floating oasis & paddleboard
Blue Dream — 54′ Jeanneau 54 DS
Experience the magic of a Caribbean sunset aboard the 54′ luxury sailing yacht Blue Dream. Cruise the calm waters around St. Thomas and St. John past secluded coves and the coastline of Virgin Islands National Park as the sky lights up in gold, orange, and pink. Relax with a premium open bar and a gourmet charcuterie board at golden hour.
- Golden-hour sail past the National Park
- Premium open bar with champagne
Blue Dream — 54′ Jeanneau 54 DS
Escape for a half day of sailing aboard the 54′ luxury yacht Blue Dream. Your captain and crew tailor the trip around snorkeling coral reefs, swimming turquoise coves, and visiting Christmas Cove — home to sea turtles, tropical fish, and the floating Pizza Pi. A smooth, all-inclusive island adventure in comfort and style.
- Premium all-inclusive open bar
- Stops at a floating pizzeria, Pizza Pi
Blue Dream — 54′ Jeanneau 54 DS
Spend a full day sailing the U.S. Virgin Islands aboard the 54′ luxury yacht Blue Dream. Your captain and crew customize the route to the best beaches, hidden coves, and snorkel spots around St. John National Park, including turtle-filled Christmas Cove. All-inclusive, with a premium open bar and a fresh gourmet hot lunch served onboard.
- Snorkel Christmas Cove with turtles
- Fresh gourmet hot lunch onboard
Start planning your perfect day on the water
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