Under sail · ST JOHN SAILING TOURS

St John Sailing Tours: Our 4 Favourites

4 sailing trips  ·  seats from $109 each

Sunset runs, swim stops and full days at anchor. These 4 are the sails in St John worth the booking, compared on the details that matter once you are aboard.

St. John Days End Sunset Sail Open Bar & Hors D'oeuvres - Westin - Champagne, open bar, and the social mood
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St. John Days End Sunset Sail Open Bar & Hors D’oeuvres – Westin

1.St. John Days End Sunset Sail Open Bar & Hors D’oeuvres – Westin

★★★★★★★★★★5.0 · 281 reviews · from $109Top of the fleet

Meet at The Westin St. John for a group sunset cruise aboard a 55-foot catamaran. You’ll sail into Pillsbury Sound with champagne, a full open bar, and passed hors d’oeuvres. The crew includes captains and attendants such as Erin, Carter, Matt, Freeman, Carolyn, and Brandon, depending on the sailing.

“Well organized and fun. Beautiful boat in pristine condition. Captain clearly knew what he was doing and was personable and skilled. The crew was great and drinks were good. Appetizers were just okay, but not the reason to go. Harbor and isRead more”

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St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin - Breakfast before the snorkeling stop
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St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast – Westin

2.St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast – Westin

★★★★★★★★★★5.0 · 176 reviews · from $299

Spend about eight hours sailing from the Westin St. John to Jost Van Dyke. You’ll have a light breakfast, snorkel near coral reefs, relax at White Bay, and visit Soggy Dollar Bar. Crews have included Captain Jolene, Riley, Eric, Brent, Dan, and Brendan, with customs handled as part of the trip.

“Great trip to BVI - snorkeling and Soggy Dollar. Crew was very friendly and met fun people on board.”

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St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin - Two water stops around St. John
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St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar – Westin

3.St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar – Westin

★★★★★★★★★★5.0 · 139 reviews · from $149

Set out from the Westin St. John at 10:15 a.m. aboard a luxury catamaran for two snorkeling stops, a beach visit, and lunch from Pizza Pi, the Virgin Islands’ floating pizza boat. The crew may include Captain Erin, Captain Emily, or Captain Wendy, with gear, towels, salads, and an open bar after snorkeling.

“No need to pack a towel. They have them for you! Pizza was great, and so were the 3 salads. Crew was super kind! I wanted to book the same one again, but hubby wanted to try something a little different haha”

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Private Day Charter Classic Sailboat - Captain Mike, Beau, and the Human Side of the Trip
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Private Day Charter Classic Sailboat

4.Private Day Charter Classic Sailboat

★★★★★★★★★★5.0 · 69 reviews

You and up to five companions sail from Cruz Bay aboard a classic 40-foot boat with Captain Mike and crew member Beau. After a tender ride to the sailboat, you’ll snorkel, swim, sunbathe, enjoy lunch and drinks, and return to the Saint John Ferry Terminal in about four to five hours.

“Once in a lifetime experience! Not only did Captain Mike teach and gave me the opportunity to sail, he brought us to a beautiful spot to snorkle! But the best was a rare experience to swim with dolphins in Scotts Bay! Incredible!!! He was as Read more”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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