Top St John Sailing

Hop aboard a 40-foot-long sailboat for this small-group sunset cruise. Your captain will take you and up to five other travelers out on a relaxing cruise through the USVI's calm waters as you watch the sun set into the sea. Free drinks and snacks onboard add to the festive, but chilled-out, atmosphere.

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.

Spend a day sailing, snorkeling, eating, and drinking with this cruise from St. John. You'll start with an on-board continental breakfast, followed by a snorkel stop at a coral reef. Then it's off to a floating taco bar, Lime Out, for lunch, followed by a bit more snorkeling before you head home.

If sailing into the sunset while sipping champagne sounds like your idea of a good time, this St. John sailing experience may be just what you need. With this group cruise, you'll sail from the Westin on St. Johns out into the Pillsbury Sound aboard a 55-foot catamaran, where you'll be served champagne and hors d'oeuvres as the sun sets into the sea.

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, our main lunch will be pizza from the Virgin Island’s ONLY floating food boat, PiZZA Pi, VI. We also include an open bar and snorkeling gear for this three-quarter day adventure. After lunch, we sail another beautiful snorkel stop for some additional snorkeling and beach time! This kid-friendly snorkeling tour in the Virgin Islands is perfect for guests of all ages!

The Picnic Snorkel Sail takes place on a luxurious catamaran, guided by knowledgeable crew. The picnic lunch being provided onboard allows for maximum snorkeling time at both of the 'off the beaten path' reef stops!

Set sail into the sunset while sipping on bubbly and snacking on hors d'oeuvres on this group cruise. You’ll hop aboard the 55-foot Daydreamer catamaran and sail off into the Pillsbury Sound, with plenty of chances to take photos or simply take in the views before you make your way back to shore.

Spend the day aboard a 40-foot sailboat with this St John day trip, departing from Cruz Bay. You'll visit a quiet cay for snorkeling and swimming before making your way to a second area for more swimming plus white-sand beach time and an included lunch before returning to Cruz Bay.

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.

Sail out to the Lovango Resort and Beach Club, on private Lovango Cay, with this evening cruise from the Westin on St. John. You’ll be served hors d'oeuvres and cocktails as you sail to the island, but you may want to save your appetite for the meal of fresh seafood that awaits you. Cordials will be served on the return trip home or you can order a drink from the on-board open bar.

Head out on a half-day adventure around St. John and nearby St. Thomas on this budget-friendly, two-stop snorkeling tour. Your captain will show you and your group of up to 48 other passengers a couple of off-the-beaten-path snorkeling spots, away from where the cruise ships frequent. Once you’ve snorkeled to your heart’s content, you can order free drinks from the boat’s on-board open bar.

Spend the day sailing in St John aboard a 40-foot sailboat with this private excursion. You'll head out to Cruz Bay where you'll take an inflatable tender out to your sailboat. You'll then head out to sea, with a couple of stops for snorkeling in the clear Virgin Islands waters.

Sail through Pillsbury Sound, with stops to visit beaches and snorkel along with colorful marine life along the way, with this private sailing and snorkeling charter for groups of up to six passengers. You'll also get to dine on an included on-board lunch, served up with cocktails, beer, wine, and soft drinks.

Set sail aboard a 60-foot sailboat with this three-hour snorkeling cruise from Cruz Bay out to Pillsbury Sound. You and your private group of up to six people will set sail aboard the Tandemeer (which once made an appearance in the film Trading Places), with a break along the way at Honeymoon Beach or Lovango Cay for swimming and snorkeling.

The best day of your Virgin Islands Vacation will be your day out sailing with Island Sailing Tours. You will enjoy the sun, wind, and water sailing out of Cruz Bay to Pillsbury Sound on the beautiful, large comfortable classic sailboat Tandemeer, which is the same boat shown in the 1980's hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis We will aslo stop at a beautiful beach and reef so you can snorkel the crustal clear waters seeing hundreds of tropical fish or swimming with sea turtles.

The best day of your Virgin Islands Vacation will be your day out sailing with Island Sailing Tours. You will enjoy the sun, wind, and water sailing out of Cruz Bay to Pillsbury Sound on the beautiful, large comfortable classic sailboat Tandemeer, which is the same boat shown in the 1980's hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis We will aslo stop at a beautiful beach and reef so you can snorkel the crustal clear waters seeing hundreds of tropical fish or swimming with sea turtles.

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 your very own sailboat here in the Caribbean. A great, hands on experience for everyone in the family and unforgettable memories with photos to prove! You are invited, though not required, to "Captain" the boat for the whole day, let everyone have a go at the helm or simply hand it back over to your guide to relax and enjoy the ride.

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!

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!

A day on the waters of the Virgin Islands aboard Asante will be the best day of your vacation. We start the day with a humorous yet informative safety talk from Captain Teddy, a beautiful fruit plate and a round of Hillary's famous rum punch. And, as we motor out of the harbor and raise the sails, conversation about St. John of past and present, the waters surrounding her, sailing, off shore adventures and day to day life will pass the time as we island hop for snorkel stops and underwater adventures! On board, you will experiences amazing snacks, drinks, comfortable bean bags on the bow, a front row seat for the views of the USVI and five star service. When we stop, you can relax in our hammock chairs, float about, snorkel, paddle board or simply relax on the boat while your loved ones enjoy the sea.

Take a half-day trip out to the waters around St. John and nearby St. Thomas by booking this two-stop snorkeling tour. Your captain will show you and your small group of fellow passengers two lesser-visited snorkeling spots, where you'll get to jump in and check out the underwater life around you. After you’re done, you can order free drinks from the boat’s on-board open bar.