8 Sailing Trips in St John Worth Booking

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

★★★★★★★★★★5.0 · 281 reviews · from $109Our pick

Board a 55-foot catamaran at The Westin St. John for a relaxed sunset cruise across Pillsbury Sound. Champagne, a full open bar, and hors d’oeuvres are included. The crew, including captains and attendants such as Freeman, Carolyn, Brandon, Erin, Carter, and Matt on some departures, keeps the evening easygoing and social.

“We decided to book the sunset cruise the last day of our trip as a closing to the vacation and so happy we did. The cruise was very nice, beautiful boat, awesome staff, food was delicious, drinks were delicious as well. The sunset was beautiful and seeing the island from a sailboat was very romantic. There were a lot of other couples on the cruise so if you are looking for a bit more privacy on a cruise tour, we recommend booking a more private option. Otherwise, we highly recommend it! The views and experience was well worth it! They make you take off your shoes on the boat, so…”

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

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

Start at 8 a.m. from The Westin St. John for an eight-hour catamaran trip to Jost Van Dyke. Expect a light breakfast, morning reef snorkeling, time at White Bay near Soggy Dollar, and a return cruise with an open bar. Crews such as Jolene, Dan, and Brendan have earned high marks for attentive service.

“Great captain and crew. So much fun on and off the boat. Crew was friendly, attentive and so much fun. The other people taking the tour were awesome tooWould do it again and again”

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

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

Sail from the Westin St. John with a friendly crew such as Captain Erin, Captain Emily, or Captain Wendy. Snorkel two sites, swim near scenic beaches, and eat hot pizza from Pizza Pi, the Virgin Islands’ floating food boat. Towels, gear, salad, snacks, and an open bar after snorkeling are included.

“Great trip excursion. Crew was great and quite friendly! Had a great time and would definitely do it again!!”

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4.Private Day Charter Classic Sailboat

★★★★★★★★★★5.0 · 69 reviews

Meet at the Saint John Ferry Terminal in Cruz Bay for a private 4 to 5-hour sail aboard a 40-foot boat. Captain Mike, sometimes joined by Beau, takes your group by tender to the sailboat, then on to two snorkeling stops, including Honeymoon Beach. Lunch, drinks, gear, WiFi, shade, and a restroom are included.

“Captain Mike is the best, thoughtful and attentive to ensure that we had a great time! He even gave my husband a sailing lesson. It was a highlight of our trip.”

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5.St. John Sail with Bar and Hors d’Oeuvres to Lovango Dinner

★★★★★★★★★★4.5 · 35 reviews · from $119

Sail from The Westin St. John to private Lovango Cay aboard a catamaran, with cocktails and hors d’oeuvres on the way out. Dine at Lovango Resort and Beach Club, then return under the stars with cordials and an open bar. Crews have included Erin, Anna, Brian, Alexi, and Riley.

“My husband and I chose this as an evening excursion while we were on our honeymoon and we truly had the best time!! The boat was beautiful and the staff was so fun, kind and attentive! It was a great way to sail through the Virgin Islands and the dinner location was absolutely beautiful! Would definitely recommend!”

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6.Group Sunset Sail St. John

★★★★★★★★★★5.0 · 31 reviews · from $400

Set sail from Cruz Bay at 4:15 pm aboard a classic 40-foot sailboat with room for up to six people. Captains Mike, Jay, Sandy, or other crew members guide you through Virgin Islands National Park with a full bar, snacks, music, and time to watch the sunset. The sail lasts about two and a half hours and returns to Cruz Bay.

“It was a great way to spend our last night on the island. It was a very nice mellow cruise. Great painkillers and some light snacks amd fun conversation the bean bag chairs at the bow were a huge hit with the ladies. Captain Mike is a really nice guy and a good sailor. We will go on his boat again.”

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7.Learn to Sail – Sailing Lessons All Inclusive

★★★★★★★★★★5.0 · 4 reviews

Spend about five hours aboard Morningstar Sailing and Power Charters’ 40-foot sailboat from Cruz Bay. Captain Mike can tailor the lesson to your group, from taking the helm to relaxing on deck. Snorkel gear, lunch, snacks, open-bar drinks, and two possible swim stops are included.

“Captain Mike tailored a great experience for us; was absolutely great with our daughter and provided a wonderful lifetime memory. The boat was sound and comfortable. If you do one excursion on Saint John's, make it a day of sailing with Captain Mike. We will do it again, for sure.”

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8.SPECIAL – (Up to 4 Passengers) All Inclusive Day Sail

★★★★★★★★★★5.0 · 3 reviews

Sail from Cruz Bay with Captain Mike and Bridget on a private five-hour trip for up to four people. You’ll visit quiet bays and beaches, snorkel with provided gear, look for sea turtles, enjoy a full deli lunch, and choose drinks from an open bar. The route stays in USVI waters.

“Captain Mike , Bridget and their little boy took us on an adventure. We sailed to the British Virgin Islands, visited Foxy's, went on to have lunch at Soggy Dollar. Yummy food and beautiful turquoise waters. Just breathtaking ! On the way there, Read more”

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