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Sailing Charters

Private catamarans, shared day sails, and everything in between. Sailing charters in the Virgin Islands deliver stunning scenery, warm water, and lasting memories.

Sunset Champagne Charter aboard a 50′ Luxury Catamaran
Seas the Day Charters

Toast the evening with two bottles of Veuve Clicquot champagne aboard S/Y Sirena, a 50-foot luxury sailing catamaran. Up to 12 guests sail toward St. John as the sky lights up at sunset, with complimentary beverages and lively music setting the mood for an evening that’s hard to top.

45′ Lagoon Luxury Catamaran Charter
Sonic Charters

Sail in style aboard a 45-foot Lagoon catamaran with a flybridge, forward sunpads, three staterooms, and a crew ready to take you through the USVI or BVI. Up to 12 guests enjoy an open bar, fresh snacks, and high-quality snorkel gear for a genuinely luxurious full-day charter on the water.

Turtle Cove Catamaran Snorkel & Sail
St. Thomas Water Sports

Sail to the uninhabited Buck Island National Wildlife Refuge’s Turtle Cove aboard a 54-foot catamaran. Snorkel alongside green sea turtles and colorful coral reefs with gear provided, or relax on the sun deck for a more laid-back Caribbean afternoon. Snacks and beverages served after the water activities.

Circle St. John & Food Boat Tour
Stormy Pirates Boat Charters

Sail a full loop around St. John with stops at the two most famous floating food boats in the USVI. Enjoy tacos from Lime Out, snorkel two pristine reefs only accessible by boat, grab pizza from Pizza Pi, and cap the day with a visit to Lovango Beach Club. Captain, mate, fuel, open bar, and pizza included.

Charlotte Amalie Harbor Sunset Sail
St. Thomas Water Sports

Two hours, one beautiful harbor, and a sunset that’ll stick with you. Sail around historic Charlotte Amalie aboard a classic catamaran with appetizers, cocktails, beer, and wine. The menu rotates with island availability, but the pirate tattoos are always on the house. Departs at 5:30pm.

Full Day Sailing Yacht Charter
Happy Island Charters

Spend a full day on a private all-inclusive charter aboard Sea Level, a classic sailing yacht with premium amenities. Enjoy the full bar, snorkel gear, a paddleboard, floating raft, Turkish towels, and an air-conditioned bathroom. Pedro the sailing dog comes along for the ride. Optional Caribbean lobster boil available.

Full Day Sailing Catamaran Charter
Seas the Day Charters

Spend a full day exploring the Caribbean aboard S/Y Mazu or S/Y Neptune, a pair of cozy 35-foot Gemini Legacy catamarans. Snorkel vibrant reefs, hop white-sand beaches, and keep watch for sea turtles and dolphins. A Fusion sound system, private bathroom, and a customizable captain-led itinerary round out this comfortable, easygoing adventure.

Sailing Yacht Sunset Sail
Happy Island Charters

Watch orange and pink light spill across the Caribbean sky from the deck of Sea Level, a classic private sailing yacht. Settle into bean bag chairs on the spacious foredeck and enjoy a curated spread of hors d’oeuvres, peel-and-eat shrimp, and sparkling wine from the premium bar. Pedro the sailing dog joins every voyage.

Champagne Sunset Sail from Margaritaville
Island Adventures – New Horizons/Breakaway/Snorkel Cat

Board a custom catamaran at Margaritaville and sail into a glowing Caribbean sunset with champagne in hand. Watch the sky shift from gold to pink to deep purple as the hors d’oeuvres are passed and Caribbean music sets the mood. An open bar featuring Painkillers, cocktails, wine, and bubbly rounds out the evening perfectly.

Snorkel Catamaran Adventure from Margaritaville
Island Adventures – New Horizons/Breakaway/Snorkel Cat

Set off from Margaritaville aboard a spacious 60-foot catamaran for a full day of snorkeling in the National Park around St. John. Enjoy breakfast, a buffet lunch, and an open bar as you explore two reef sites in brilliant Caribbean waters. Shaded decks, sun lounges, and restrooms on board.

Private Sunset Sail & Snorkel
Stormy Pirates Boat Charters

A private sunset sail and snorkel on a beautiful sailing catamaran, complete with a full open bar and sparkling wine included. Watch the Caribbean sun paint the sky from the water, snorkel the warm sea, and enjoy the kind of 360-degree sunset view that only happens out on the water. Perfect for couples and families.

Do It All Trip: Snorkel, Pizza and Sunset
Ocean Surfari

The Do It All Trip lives up to its name. Hit two National Park snorkel sites around St. John, eat fresh pizza from Pizza Pi at Christmas Cove, and then dance into the sunset on an open bar party cruise aboard the Reef Surfari. All gear, pizza, and drinks included in one epic 5.5-hour adventure.