Top St John Sailing Trips

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half or full day charter. Visit the islands and harbors of St. Thomas, St. John or the exciting isles of the BVIs.Seas the Day's 50′ Luxury Voyage Catamaran has a spacious salon and galley that opens on to an expansive back deck with comfortable seating and dining. The bow of the boat offers relaxing seating with bean bag chairs and two large trampolines for group conversations, breezy tanning or intense turtle, dolphin and whale watching. There are plenty of water toys to keep you entertained throughout the day, from SUP’s, snorkeling equipment and relaxing floats to beach games. Price includes ice, soda, beer, rum punch and light snacks. You and our captain will design an itinerary that best meets the needs of your group. Please note, some BVI destinations are w/ full day charters only. Yacht departs from Jimmy Buffett's Margaritaville Restaurant.

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. We are a classic sailing company that wants you to experience the purist's art of sailing while enjoying the surrounding scenery, fresh air, open bar and light fare.

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all group charters. Allow us to show you our BVI playground. Spend the day relaxing under the coconut trees while sipping on a painkiller!!

Escape the tourist crowds and explore the US and British Virgin Islands at your own pace on a private boat excursion from St. John or St. Thomas. Sunbathe on the boat’s deck, snorkel and swim in the refreshing waters, or island hop for an intimate sightseeing experience, benefiting from insight and tips provided by your captain on a fully customizable tour.

ReAction is a spacious, stable and comfortable yacht. She sails like a dream, and gets guests to their destination quickly. She is loaded with watersports toys that will entertain children and adults alike! We offer 3 different itineraries, with flexible pickup and drop off times and locations. The perfect adventure for families and friends! We also offer SCUBA diving excursions upon request, as well as rock climbing and cliff jumping packages. Come and enjoy the highlight of your vacation with us!

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 dazzling white sandy beaches lapped by tranquil, clear turquoise waters. This can include exploring many of the Islands and Cays in the Virgin Islands, all excellent snorkeling spots teeming with fish and coral. Your lunch is included with beverages and very open bar!

Large catamarans are fast and stable. Great way to sail. The power boat is used if you just want to go over to the Lime Out bar and snorkel a little bit. The Trimaran is used for teaching how to sail and you can take it out alone if you have experience.

Cloud 9 is a large sailing Yacht that caters to small groups. Cloud 9 has 15 years experience sailing from St John, so we know all the best spots. Your licensed Captain and Crew will entertain you with stories and spoil you with service. Our private trip price allows you to take up to 8 people!

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands.

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 cruise port and to taxi and catch the commuter ferry ($8.00). The ferry takes 12 minutes and shows you more of the surrounding cays in transfer. Your crew will be waiting for you as you arrive on the beach immediately off the dock from the ferry. Here you will board our inflatable tender and to be delivered to our very calm anchorage and all inclusive sailboat. We've been sailing here for nearly 18 and our itinerary showcases the true home of the islands culture and island vibration we believe our guests are looking for. St. John's protected western shoreline provides the perfect venue for our guests to enjoy the serene, blue, waters to relax and sunbathe or take the helm of 40 ft sail boat. We offer our guests the chance to swim with amazing sea life and comb the white sandy beaches of some of the most incredible shoreline on the planet.

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 swim with sea turtles daily. We look forward to sharing our passion for true sailing, hospitality and the best day of your vacation with you!

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 dazzling white sandy beaches lapped by tranquil, clear turquoise waters. This can include exploring many of the Islands and Cays in the Virgin Islands, all excellent snorkeling spots teeming with fish and coral. Your lunch is included with beverages and very open bar!