St John Sailing

Wayward Sailor - We specialize in sailing. As a 35 year Caribbean sailor, we only run the engine when we have to.

Wayward Sailor offers charters to the U.S. Virgin Islands (USVI) and British Virgin Islands (BVI). Visit Foxy's in the BVI, the US Virgin Islands National Park (VINP), St. John Natural adventure and environmental education for your family.

Bread on the Water - Sailing the beautiful turquoise waters around St. John (see map) and the other Virgin Islands is a great way to enjoy the spectacular beauty of the islands and see the lovely beaches and coves of the Virgin Island's National Park as well as the smaller outlying islands.

Breath is a one-of-a-kind, hand-built, gaff rigged, small tall ship. When they talk about a boat with character, this is what they mean. She stands out from the crowd. Breath is not just another tourist boat. She’s a real ship with a colorful history. Breath is the biggest boat ever to be built on St. John, USVI and over the last 20 years has become a part of St. John’s sailing lore.

Cloud 9 Sailing Adventures - Cloud 9 Sailing Adventures offers full day or half day sail and snorkel trips, Jost Van Dyke day trips, sunset sails, and custom charters. And, check out our new afternoon/sunset/lobster dinner trip to Sidney's and White Bay on JVD offered only by Cloud 9.

We offer snorkel stops at the best sites, selected to fit your interest and experience level. Cloud 9 is the only day sail charter boat that now offers scuba diving. Captain Jason has more than 30 years of extensive sailing experience. Our goal is to make your sailing trip with us the best part of your vacation.

St. John Yacht Charters

Local Waters Day-sail - (9:30-3:30) Our Local waters day-sail trip is all inclusive with two snorkel stops around St. John and some of the beautiful surrounding U.S. islands. We eat a gourmet, deli/style lunch after our 1st snorkel stop that is served out in our spacious cockpit area.

After our second snorkel stop in a different location we have a snack and drinks (water, rum drinks, soda, beer) then we get ready for our sail back. You will love sailing around St. John on Survivan and snorkeling some of the most beautiful spots in the world! This is a fun trip for the family! You can't beat Sailing, Snorkeling, and Relaxing on the Sailboat Survivan.

Half Day, A three-hour Sailing/Snorkel tou - We go either 9:00 am to 12:00 pm or 1:00 pm to 4:00 pm. This trip is around St. John with one snorkel stop (typically Little St. James or Henley Cay) but it always depends on the wind and seas.

Sunset Sail - This is a two hour tour that sails out around 4:30 depending on the time of year. We enjoy wine, along with the sunset and some fabulous appetizers. We also have our standard open bar available on this trip as well.

Jost Van Dyke - We sail at 9:00 and get back usually around 4:30. We sail over to snorkel at Henley Cay and then head over to Great Harbor. We check into customs and check out the gift shop, then the best part is heading over to beautiful White Bay & the famous Soggy Dollar Bar! We eat lunch ashore, basking in hammocks, drinking the Jost Van Dyke special known as the "painkiller". You may never want to leave.

We also offer another Jost trip that goes to Sydney’s Peace & Love, for Lunch. Here they serve Caribbean Lobster and BBQ. Then we head over to play on Sandy Cay. 8:30 am to 4:30 pm.

You must have a valid passport for these trips.

Cruz Bay Watersports - Island Spirit is a brand new custom built sailing catamaran. The vessel is 60 foot long 30 feet wide and U.S. Coast Guard certified for 70 passengers. This vessel is unique and the first of its kind in the US Virgin Islands. It was designed for comfort underway and easy water access at anchor or from the beach.

Outlaw - Our Baltic 55 is U.S. Coast Guard certified for your group of up to 12.

Half Day Sail
Explore the endless horizon of small cays surrounding St. John, Lovango/Congo, Henley, Whistling, St. James. Outlaw offers the perfect panorama for an exciting 3 hour cruise or stop at one of their fringe reefs for unspoiled snorkeling. Beverages and snacks are included.

Full Day Sail
Experience Outlaw's windward performance to whatever anchorage suits your tastes for pristine beaches, reef snorkeling, gourmet lunch and a relaxing return, reaching downwind. St. John's north shore offers vistas of the British Virgin Islands as you tack through Sir Francis Drake Channel, with historic ruin exploration and great snorkeling at Leinster Bay. The south shore opens new frontiers on the Caribbean's edge with remote anchorages.

Sail Safaris - Our sailing tours are like nothing you've ever experienced before. We are focused on getting off the beaten track. We go to hidden beaches, uninhabited islands and vibrant coral reef. So bring your snorkel gear, an appetite for adventure and dress to get wet.

Sail St. John - Offering day, half-day, sunset sails, private charters, motor excursions, weddings-on-board and a variety of other on the and in the water activities for Caneel Bay Resort and St. John guests.

St. John Sailing - St. John sailing, St. John snorkeling and explore in US and British Virgin Islands on Catamaran Calypso. Plan the perfect day by taking your family and friends for any of our half day and full day sails that depart from St. John.