Top St John Sailing Tours

Learn to sail across the azure waters of the Caribbean Sea with this private sailing lesson in St. John. Board your vessel with your group and “captain” your boat for the whole day, or relax on the decks. Your day includes swim and snorkel stops, deli sandwiches, snacks, mixed drinks, beer, soda, juice, and water.

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, as the sun sets into the sea.

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!

Spend about 6.5 hours 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 full open bar on the catamaran after snorkeling and more snorkeling before you head home. Weather conditions determine if sailing is an option.

Make a day trip to Jost Van Dyke from St. John that maximizes your time, combining several activities in one excursion. Enjoy a light continental breakfast during the cruise, go for a morning snorkel near the coral reefs surrounding the island, and relax at White Bay beach near the famous Soggy Dollar Bar with a full open bar available on the return cruise.

No need to suffer through a stale packed sandwich on this full-day snorkeling cruise. Instead, enjoy freshly-made pizzas from the unique floating food boat Pizza Pi. Spend the rest of the day working up an appetite with swimming and snorkeling at picturesque beaches and offshore cays. When you’re tired from all that swimming, relax on deck and make the most of the free snacks and open bar.

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 the water and multiple options for destinations as well. St. John's protected western shoreline provides the perfect venue for your entire party to enjoy the serene, blue, waters to relax and sunbathe while we set a course to show you sea turtles up close! At this first stop you will be fitted with the equipment needed to enjoy amazing snorkeling. (Snorkeling equipment is included in your day with us also). After snorkeling and swimming for approximately 40 minutes, we will head to a second stop where you will be able to swim with more amazing sea life and comb the white sandy beaches of some of the most incredible shoreline on the planet. You decide where you’d like to enjoy lunch because you have the boat exclusively to yourselves!

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.