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5 Fun Sailing Tours on St. John, USVI

Looking for a sailing adventure in the US Virgin Islands? These are our top picks for the best sailing tours on St. John!

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Want to sail on St. John?

Sailing in the US Virgin Islands is essentially a right of passage. It’s what makes this destination so cool and unique. The winds blow steadily, the waters are pristine, and you’ll find enough calm bays and coves to rest for a while. Not to mention the epic snorkeling opportunities along any shoreline.

That’s why I always recommend anyone who visits the Virgin Islands to hop on a boat in some capacity. For us, that’s often hopping aboard a vessel to go scuba diving around St. Thomas. But other days we try our hand at sailing. And when we do, we prefer the sights of St. John and Virgin Islands National Park.

Just see for yourself:

Although we were aboard my buddy’s vessel in the video above, there are quite a few options for a sailing tour on St. John to do a similar trip. The rest of this article highlights some of the top sailing tours on St. John in the US Virgin Islands.

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Sailing Charters on St. John, USVI

Sunset Sail With Cruz Bay Watersports

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Departing the Westin on St. John, you’ll board a massive catamaran for a smooth sailing adventure as the sun sets over St. Thomas. Day trips aboard this same vessel bring passengers to Coral Bay for snorkeling in Hurricane Hole followed by a lunch stop at Lime Out VI – the Caribbean’s only floating taco stand.

🌮 Floating Taco Stand: Lime Out VI is a wild experience in Coral Bay as you swim up to the bar to order a rum cocktail and delicious tacos. Check out our article on how to get there to see what your best option is.

Small-Group Sail to St. John from St. Thomas

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Virgin Islands Day Sailing departs St. Thomas every day for a trip to St. John and the surrounding waters of Virgin Islands National Park. It’s a semi-private excursion with a limited amount of space with a pleasant Captain and crew!

Sail, Snorkel With Sea Turtles, and Stop at a Pizza Boat

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Snorkeling with a green sea turtle on St. John

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Stormy Pirates departs St. Thomas aboard their catamaran as they head to Maho Bay for snorkeling with sea turtles before dropping anchor in Christmas Cove to visit a pizza boat known as Pizza Pi. The pizza boat experience is worth the trip alone as Pizza Pi delivers the pizzas directly to your boat via dinghy!

🤿 Snorkeling with Sea Turtles in the US Virgin Islands: Another great place to go snorkeling with sea turtles is Brewers Bay on St. Thomas. Be sure to check it out on your trip!

Sunset Sail from St. Thomas

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Laura aboard a large catamaran on St. Thomas

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The Lady Lynsey is one of the most iconic sailing vessels in the US Virgin Islands as it departs the Ritz-Carlton on St. Thomas. This sunset dinner cruise will serve up appetizers and cocktails as it heads to St. John where you’ll unload to eat dinner on your own. At the end of the evening, you’ll board again to head back to St. Thomas while the crew serves dessert aboard the vessel.

All-Inclusive Private Day Sail

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Consider hopping aboard this all-inclusive sailing vessel for a private experience for your entire family or small group. Drinks and food are included as you sail along the pristine north shore beaches of St. John and beyond. Request stops at Maho Beach and Waterlemon Cay for some snorkeling!


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Check out More Sailing in St. John on Youtube!

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Read More Ocean Adventures!

We hope you enjoyed our post on sailing on St. John, USVI. Hopefully, you’ll find it helpful on your next adventure! Here are a few more ocean-loving articles we think you should read next:


Have you been sailing around St. John and the US Virgin Islands before? How was your experience? What other companies or vessels should we include on our list? Are these the best sailing tours on St. John? Let us know in a comment below!

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