Couples Getaway Charters in St. Thomas & St. John

Discover St. Thomas and St. John aboard Cruzomian, a nimble 32′ Intrepid perfect for families and groups. Snorkel the reefs and turtle spots around St. John National Park, swing by Christmas Cove for Pizza Pi, and unwind on a quiet beach. Twin 300 Yamahas and a kid-friendly layout make for a smooth, easy day on the water.

Get the best of both worlds aboard Kindred Spirit II, a 46′ Leopard sailing catamaran, on a full afternoon of island adventure that rolls right into a Caribbean sunset sail. Snorkel reefs, paddleboard turquoise bays, and beach-hop to spots like Lovango or Christmas Cove, then settle in as the sky lights up over St. Thomas and St. John.

Explore the British Virgin Islands aboard Cruzomian, a nimble 32′ Intrepid built for families and groups. Snorkel the Caves and the Indians at Norman Island, float up to the Willy T and Soggy Dollar Bar, and finish among the granite boulders of The Baths at Virgin Gorda. Twin 300 Yamahas and a smart, kid-friendly layout keep the day smooth.

Sail away on our full-day trip aboard our luxury 55-foot sailing catamaran for a day of snorkeling the pristine waters of the Virgin Islands National Park and fun on the island of Jost Van Dyke - the home of the world-famous Soggy Dollar Bar.

Sail aboard Lady Lynsey II into the Virgin Islands National Park for an unforgettable snorkel adventure with green and hawksbill sea turtles. Enjoy two snorkel stops, a picnic-style lunch on board, and an open bar before a scenic downwind sail home to the beaches of The Ritz-Carlton.

Toast golden hour aboard Kindred Spirit II, a 46′ Leopard sailing catamaran, on a relaxed 2.5-hour private sunset sail. Cruise the calm waters around St. Thomas and St. John with handcrafted cocktails, beer, and prosecco in hand and a gourmet charcuterie board to share as the sky fills with Caribbean color.

Join this top rated luxury sailing catamaran for a snorkel adventure and lunch at Lime Out, the only floating taco bar in the Virgin Islands. Enjoy an offshore reef snorkel followed by a two-taco lunch and open bar before a leisurely downwind sail home.

Spend a full day in refined comfort aboard Enchantment, a spacious 58′ Viking Princess. Lounge across the large cockpit, aft sun pad, and bow seating, or escape the heat in the fully air-conditioned interior with a galley and full bathroom. Your captain and crew tailor the route to the day's conditions and your group's interests.

Sail away on our full-day trip aboard our luxury 55-foot sailing catamaran for a day of snorkeling the pristine waters of the Virgin Islands National Park and fun on the island of Jost Van Dyke - the home of the world-famous Soggy Dollar Bar.

Two-hour Sunset & Harbor Lights Dinner Sail departing from Marriott's Frenchman's Cove. It features spectacular Caribbean sunset views, an open bar, and freshly prepared, island-inspired dinners.

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.

Climb aboard the Taco Tug, a one-of-a-kind restored 1980s U.S. Navy lifeboat turned island adventure boat — one of the most unique trips in St. Thomas. This relaxed small-group cruise from Crown Bay heads to Honeymoon Beach on Water Island to snorkel with sea turtles, then over to the famous Lime Out floating taco bar for handcrafted tacos and cocktails.

Take on the British Virgin Islands aboard New Magic, a comfortable 50′ Sea Ray Sundancer. Snorkel the Caves, float up to the Willy T and Soggy Dollar, and finish at The Baths on Virgin Gorda. Stretch out on the bow sun pad when you want sun, or duck into the air-conditioned cabin when you don't.

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.

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.

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.

Spread out aboard Freedom, a 45′ Lagoon flybridge catamaran with shade, sun, and space to spare. Lounge on the bow trampolines, claim the breezy flybridge seat next to the captain, or relax in the indoor salon. Your captain and crew shape the day around St. John National Park, Christmas Cove, and the reefs in between.

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.

Explore the British Virgin Islands aboard Moca, a fast 37′ Intrepid center console for up to 12 guests. Snorkel the Caves, float up to the Willy T and Soggy Dollar Bar, and finish among the boulders of The Baths at Virgin Gorda. Triple 350 Yamahas and a roomy bow make island hopping smooth and easy.

Cover more ground aboard Izulu, a fast 37′ Intrepid powerboat built for island hopping around St. Thomas and St. John. With twin 300HP Yamahas, your captain can reach more spots in a day — St. John National Park, Lovango, Lime Out, Pizza Pi, and secluded beaches. A dive door and freshwater rinse make the water easy for everyone.

Snorkel with sea turtles aboard VI Cat, a spacious 54′ Gold Coast catamaran, on a three-hour shared sail to Turtle Cove at Little Buck Island National Wildlife Refuge. Swim among green sea turtles, tropical fish, and coral with gear and beginner guidance provided — the most accessible turtle experience in St. Thomas.

Discover St. Thomas and St. John aboard Moca, a fast 37′ Intrepid center console for up to 12 guests. Snorkel the reefs around St. John National Park, swing by Christmas Cove for Pizza Pi, and relax at a quiet afternoon beach. Triple 350 Yamahas and a roomy layout keep the day smooth for the whole group.

Set sail on the luxurious Flying Frenchman for an exhilarating snorkel adventure along the south shore of St. Thomas. Enjoy two off-the-beaten-path snorkel stops, a curated tapas-style lunch on board, and an open bar for the perfect day on the water.

Combine a full afternoon of adventure with a golden-hour sail aboard Intrepid, a sleek 2022 Fountaine Pajot Astrea catamaran. Snorkel reefs, paddleboard calm bays, and beach-hop around St. Thomas and St. John, then unwind for a sunset sail. Cool off in the air-conditioned interior and stay connected with onboard Starlink internet.

Set sail into the sunset aboard VI Cat, a spacious 54′ Gold Coast catamaran, for a two-hour shared dinner cruise off St. Thomas. Cruise Charlotte Amalie Harbor and the coastline as the sky turns gold, with a full island-inspired dinner and drinks served onboard. The only catered sunset dinner sail in the fleet — ideal for date nights and celebrations.

Unwind into golden hour aboard Sail Meow, a spacious 44′ Leopard catamaran, on an intimate two-hour sunset sail around St. Thomas and St. John. Lounge in sun or shade with a cocktail in hand as warm Caribbean breezes and sunset colors roll across the water.

Bad Kitty and Bad Kitty 2 are 49′ wave-piercing power catamarans built to provide speed, comfort, and your choice of sun or shade. Their design provides the smoothest ride possible. Enjoy the comfortable ride on the top sun deck or open stern seating.

Toast the evening aboard Sweet Pea, a luxurious 40′ Voyage catamaran, on a two-hour private sunset sail through the U.S. Virgin Islands. Sip champagne and cocktails with hors d'oeuvres as the Caribbean sky turns gold — an intimate evening that feels private even with the whole group aboard.

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.

Enjoy a golden-hour sail aboard Intrepid, a sleek 2022 Fountaine Pajot Astrea catamaran. Enjoy a glass of chilled champagne along with a gourmet charcuterie board. Allow the sounds of the sail, wind and water to bring a peaceful and memorable end to your day.

Join this top rated luxury sailing catamaran for a snorkel adventure and lunch at Lime Out, the only floating taco bar in the Virgin Islands. Enjoy an offshore reef snorkel followed by a two-taco lunch and open bar before a leisurely downwind sail home.

Cruise St. Thomas and St. John aboard New Magic, a comfortable 50′ Sea Ray Sundancer. Snorkel the reefs around St. John National Park, stop at Christmas Cove for Pizza Pi, and wind down at a quiet beach. Lounge on the bow sun pad or cool off in the air-conditioned cabin between stops.