Milestone Celebration Charters in St. Thomas & St. John

Cruise St. Thomas and St. John aboard Ramble On, a powerful 43′ Formula SSC built for a fast, smooth ride. Spend the day snorkeling coral reefs, swimming hidden coves, and island hopping to spots like Pizza Pi and Lovango — then retreat to the air-conditioned cabin between stops. Your captain and crew deliver first-class service all day long.

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.

Explore the British Virgin Islands aboard Ramble On, a powerful 43′ Formula SSC built for speed and comfort. Visit iconic spots like the Soggy Dollar Bar, the Willy T, The Indians, and The Baths at Virgin Gorda, with snorkeling and beach hopping in between. Quad 350HP engines deliver a smooth, effortless ride for up to 12 guests.

Explore St. Thomas and St. John aboard Maverick, a fast 2023 39′ Nor-Tech powerboat. Swim with sea turtles, stingrays, and reef fish over coral gardens and shipwrecks, then pull up to floating spots like Lime Out, Pizza Pi, and Dinghy's on Water Island. The electric canopy and modern amenities keep the day comfortable and quick between stops.

Spend a full day exploring St. John and the USVI aboard Sunny Daze, a custom 36′ Aventura power catamaran built for a smooth, dry ride. Snorkel vibrant reefs, swim turquoise coves, and pull up to island beach bars like Lime Out and Pizza Pi. With high sides, a wide open deck, and a bow lounge that converts to beds, there's room for up to 12 to spread out.

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.

Chase the best of the British Virgin Islands aboard Maverick, a fast 2023 39′ Nor-Tech powerboat built for speed and modern comfort. Cruise to The Baths at Virgin Gorda, Sandy Cay, and Oil Nut Bay, snorkel The Indians and The Caves, and pull up to beach bars like the Soggy Dollar and Willy T. An electric canopy keeps the aft lounge shaded all day.

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.

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

Set out for a full Caribbean day aboard Sail Meow, a luxury 44′ Leopard catamaran. From the east end of St. Thomas, snorkel reefs full of turtles at Christmas Cove, lunch at Scott Beach, and cruise the back side of Lovango. With a chef onboard and a dinghy to ferry you ashore, it's adventure and ease in one.

Cruise the British Virgin Islands aboard Sunny Daze, a custom 36′ Aventura power catamaran built for a smooth, dry ride. Stop at White Bay on Jost Van Dyke, snorkel caves and reefs, and relax on white sand beaches with oceanfront lunch views. With a wide open deck and seating for up to 12, there's room for the whole group.

Explore the U.S. Virgin Islands aboard Ocean Breeze, a fast 35′ Contender built for island hopping. Cruise the reefs around St. John National Park, stop at Christmas Cove for Pizza Pi, and relax on pristine white sand beaches. Twin 300HP engines and a big shaded hardtop keep the ride smooth for up to 10 guests.

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.

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.

Cross to the British Virgin Islands aboard Northside, a high-performance 37′ Axopar built for fast, smooth cruising. Depart the USVI and spend the day at Jost Van Dyke, Norman Island, Virgin Gorda, and The Baths — snorkeling reefs, swimming turquoise coves, and stopping at beach bars like the Soggy Dollar and Willy T.

Chase the best of the British Virgin Islands aboard Ocean Breeze, a 35′ Contender built for speed and island hopping. Run out to White Bay on Jost Van Dyke, snorkel caves and reefs, and pull up to beach bars and floating restaurants across the BVI. Twin 300HP engines and a big shaded hardtop keep the ride smooth and comfortable for up to 10 guests.

Spend a relaxed Caribbean afternoon aboard Sail Meow, a spacious 44′ Leopard catamaran. Departing the east end of St. Thomas, you'll snorkel Christmas Cove among reef fish and sea turtles, grab a slice at Pizza Pi if you like, then unwind at Scott Beach on St. John. An onboard dinghy ferries you to shore — little to no swimming required.

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.

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.