This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group charters. After checking in at the Westin on St John, guests board our 55′ catamaran for a truly extra... More

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at Lime Out, the only floating taco bar in the Virgin Islands and listed on Time magazine’s 2019 li... More

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full sail aboard our 55′ catamaran, Daydreamer. Enjoy a relaxing and romantic sail in ... More

You will have private, personable and unique experience with Sailing Tipitina. We are owner/operators and live aboard this classic sailboat with our sweet Weimeraners Oyster and Pearl.... More

If you are looking for a curated, private sailing experience, our goal is to not only meet, but to exceed your expectations. We will welcome you aboard with fresh fruit & muffins to discuss the days itinerary and to plan the day o... More

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful and authentic day at sea. We offer snorkeling options for all skill levels and swi... More

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies,... More

The private island escape of Lovango Resort + Beach Club is the newest go-to destination in the USVI. Enjoy an unforgettable waterfront meal with breathtaking views looking out over Pillsbury Bay with St. John in the distance, whi... More

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time on the water? Join us for our all inclusive private day sail adventure as well! ... More

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full sail aboard our 55′ catamaran, Daydreamer. Enjoy a relaxing and romantic sail in ... More

Sailing on Helios in the Virgin Islands can be one of the most memorable days spent on your vacation. The Virgin Islands are a popular destination for sailors, with near-constant trade winds, all-year round high temperatures and ... More

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy ports of St Thomas to meet near the commuter ferry terminal in Cruz Bay. The ferry ta... More

Snuggle up with our boat dogs, Oyster and Pearl, on our comfy bean bags as you watch the sunset. Our sailboat is a 43' Hans Christian, she is a true classic sail yacht which is meticulously maintained and a real head turner. Come ... More

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing. We can offer as much or as little instruction as you request while you take the helm of y... More

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful and authentic day at sea. We offer snorkeling options for all skill levels and swi... More

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful and authentic day at sea. We offer snorkeling options for all skill levels and swi... More

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty of the Virgin Islands, particularly St John. Departing from Cruz bay allows us a wonderful day on ... More