Virgin Islands · SAILING

The 15 Best Sailing Trips in the Virgin Islands

39 tours  ·  from $70 a head

Steady trade winds, short crossings and an anchorage every few miles: this is why people learn to sail here. The 15 below cover half-day sails, full days with lunch and the crewed charters, priced per head where the boat allows it.

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - Boarding at Frenchman’s Cove
Sailing, Snorkeling, Tour Reviews, Tours in St Thomas, Turtle Snorkeling

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

1.Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

★★★★★★★★★★5.0 · 2,100 reviews · from $119Our pick

Spend three hours aboard The VI Cat, sailing from Marriott Frenchman’s Cove to Turtle Cove at Little Buck Island. Crew members such as Captain Serena, Nick, Isaac, and Porscha help with safety, snorkeling, and drinks. Equipment, snacks, and post-swim alcoholic drinks are included, with time to swim or relax onboard.

“Fun, easy going trip to see amazing turtles feeding on grass and rising to the surface for air. Also a coral reef with plenty of fish and colors.”

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Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - Boarding at Marriott Frenchman’s Cove
Dining Experiences, Dinner Experiences, Sailing, Sunset Sails, Tour Reviews, Tours in St Thomas

Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

2.Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

★★★★★★★★★★5.0 · 1,176 reviews · from $119

Board The VI Cat at Marriott Frenchman’s Cove for a two-hour sunset and harbor lights sail. Enjoy tacos on Tuesdays or barbecue on Wednesdays, Fridays, and Saturdays, along with alcoholic and non-alcoholic drinks. The spacious 54-foot catamaran offers open-air seating, island views, and a relaxed social atmosphere.

“The sunset cruise was exactly the kind of experience that stays with you. The crew made everything smooth and easy, and the vibe on board was relaxed but fun. Watching the sky shift from gold to deep purple over the water felt like a perfRead more”

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Champagne Sunset Sail from Margaritaville - Champagne, Painkillers, and the open bar
Sailing, Sunset Sails, Tour Reviews, Tours in St Thomas

Champagne Sunset Sail from Margaritaville

3.Champagne Sunset Sail from Margaritaville

★★★★★★★★★★4.5 · 691 reviews · from $130

Set sail from Frydendal at 4:30 p.m. aboard a new catamaran for roughly two hours of coastline views, sunset, and moonrise. Your ticket includes champagne, wine, cocktails, Painkillers, rum punch, soda, heavy appetizers, and an onboard restroom. Crew members such as Big Tuna, Danny Boy, Carolina, and Dawn may help make the evening lively and personal.

“This was the most amazing experience for our girls trip! Everything was clean, the food was amazing, and the service was excellent, we loved Noelle and the crew! ✨ thank you!”

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St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max - Sailing toward St. John National Park
Full-Day, Sailing, Snorkeling, Tour Reviews, Tours in St Thomas

St John & Surrounding Cays – Full-Day Sail/Snorkel, 6 Guests Max

4.St John & Surrounding Cays – Full-Day Sail/Snorkel, 6 Guests Max

★★★★★★★★★★5.0 · 635 reviews · from $245

Leave Sapphire Beach Marina at 9:00 a.m. for a small-group sail toward St. John National Park and nearby cays. Captain Kendall, Addison, Tommy, Mark, Rusty, Sam, or Gabi may guide the day, with two or three snorkel stops, lunch, an open bar, and gear included. Routes change with wind, weather, and boat traffic.

“Great excursion. Nice way to see the islands. Mark and Rusty did a fantastic job of telling us about the islands, stopped at two locations to snorkel. Small group of 6 which made it really nice. Highly recommend”

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Half Day Luxury Catamaran Turtle Snorkel And Beach - Snorkeling near Buck Island National Wildlife Refuge
Beach Excursions, Sailing, Snorkeling, Tour Reviews, Tours in St Thomas, Turtle Snorkeling, VIP

Half Day Luxury Catamaran Turtle Snorkel And Beach

5.Half Day Luxury Catamaran Turtle Snorkel And Beach

★★★★★★★★★★5.0 · 635 reviews · from $159

Join Captain Joe and Catie on the Someday, a modern catamaran limited to 12 people. Snorkel near Buck Island National Wildlife Refuge, look for green sea turtles and colorful fish, then relax at Honeymoon Beach on Water Island. Gear, snacks, fresh water, and drinks are included.

“The captain and his first-mate were very friendly and informative about the surroundings! We had a great time and would highly recommend Catie and Joe as captains!”

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50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience - Secret Harbour and the east end of St. Thomas
Beach Excursions, Private, Sailing, Snorkeling, Tour Reviews, Tours in St Thomas, VIP

50′ Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

6.50′ Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

★★★★★★★★★★5.0 · 606 reviews

Take a private 50-foot catamaran from Red Hook for four to seven hours around St. Thomas, St. John, and nearby cays. Your captain, often including crew such as Maddy, Alex, JW, or Dave, helps shape the route around snorkeling, beaches, and lunch. The boat carries up to 12 people and includes floats, snorkel gear, water, soda, beer, and rum punch. BVI trips are not available.

“Dave was very knowledgeable and a great host. Highly recommended! Will use again next time we return for sure!”

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Sunset Sail with Cocktails and Appetizers - Boarding at Marriott’s Frenchman’s Cove
Sailing, Sunset Sails, Tour Reviews, Tours in St Thomas

Sunset Sail with Cocktails and Appetizers

7.Sunset Sail with Cocktails and Appetizers

★★★★★★★★★★5.0 · 580 reviews · from $95

Sail Charlotte Amalie Harbor aboard the 54-foot VI Cat from Marriott’s Frenchman’s Cove. Your two-hour trip includes cocktails, wine, beer, soft drinks, fruit, vegetables, hummus, pita, cheese, meat, chips, and salsa. Crews may include Captain Serena, Captain Michael, Isaac, Nick, Portia, or Adrienne. Arrive 30 minutes early because late boarding is not allowed.

“Me and my friend loved it! Boat was beautiful, the views, and our pictures came out amazing. Loved the painkiller and the appetizers. I would definitely do it again if I came back!”

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Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. - Building your route around snorkeling and beach time
Beach Excursions, Boat Charters, Private, Sailing, Snorkeling, Tour Reviews, Tours in St Thomas, VIP

Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

8.Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

★★★★★★★★★★5.0 · 386 reviews

Set sail from Havensight aboard S/Y Pisces, a 47-foot Leopard catamaran with room for up to 12 people. Your captain and first mate can shape the day around snorkeling, turtle watching, beach time, island views, and music from your phone. Beer, rum punch, soda, water, floats, snorkel gear, and a restroom are included.

“Our captain Ann Marie and her crew were amazing and made our experience on the boat perfect! Thanks again!”

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Live Music Sunset Sail - Frederiksted waterfront and Sandy Point
Concerts, Sailing, Sunset Sails, Tour Reviews, Tours in St Croix

Live Music Sunset Sail

9.Live Music Sunset Sail

★★★★★★★★★★5.0 · 285 reviews · from $70Best value

Sail from Frederiksted Pier for about 2.5 hours aboard a catamaran with live local music, complimentary Cruzan rum punch, and views of the west coast at sunset. You may spot sea turtles or dolphins, look for the green flash, and pass Sandy Point National Wildlife Refuge. Shoes come off, and the boat holds up to 48 people.

“The crew, music, and views of the island and sunset were amazing! We highly recommend the music sunset cruise!”

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Half Day Sail and Snorkel with the Turtles - Reaching Turtle Cove at Buck Island
Sailing, Snorkeling, Tour Reviews, Tours in St Thomas, Turtle Snorkeling

Half Day Sail and Snorkel with the Turtles

10.Half Day Sail and Snorkel with the Turtles

★★★★★★★★★★5.0 · 285 reviews · from $140

Captain Mike and first mate Nikki take you from Charlotte Amalie aboard Fury, a restored sailing yacht bound for Turtle Cove at Buck Island. Expect a short snorkel lesson, calm water, green sea turtles, tropical fish, octopus, and stingrays, followed by drinks and snacks. The boat carries no more than 25 people.

“Very easy going, relaxing tour and snorkeling. The crew is great, we got to swim with a turtle. This was our second trip with them. We were happy customers!”

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St. John Days End Sunset Sail Open Bar & Hors D'oeuvres - Westin - The sunset route from Cruz Bay
All-Inclusive Day Sails, Drinking Tours, Sailing, Sunset Sails, Tour Reviews, Tours in St John

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

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

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

Board a 55-foot catamaran at The Westin St. John for an evening cruise into Pillsbury Sound. Champagne, a full open bar, and passed hors d’oeuvres are included. The crew, including captains such as Freeman and team members Erin, Carter, Matt, Carolyn, and Brandon, keeps the mood relaxed. Expect a social group sail, not a private charter.

“The boat has a no shoes policy. Wear easily removable shoes. The crew was great and weather perfect.”

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Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX - Leaving Sapphire Beach Marina
Sailing, Snorkeling, Tour Reviews, Tours in St Thomas

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

12.Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

★★★★★★★★★★5.0 · 226 reviews · from $159

Join Captain Rob and Deb aboard the sailing vessel Cosmos Mariner for a three-hour trip from Sapphire Beach Marina. With no more than six people, you’ll sail toward Caneel Bay or another calm nearby cove, then snorkel among tropical fish, turtles, rays, starfish, coral, and possibly a shipwreck. Gear, snacks, soft drinks, and alcohol are included.

“This is a Very Well run operation. Captain Rob and Deb are great hosts. The 1/2 day sail and snorkel was a great way to do spend an afternoon.”

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Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim - Trunk Bay, Scott Bay, Maho Bay, and Magens Bay
Beach Excursions, Island Hopping, Powerboat Charters, Private, Sailing, Snorkeling, Tour Reviews, Tours in St Thomas

Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

13.Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

★★★★★★★★★★5.0 · 207 reviews

Charter the 36-foot MV Poseidon from Red Hook for 4 to 7 hours with up to 12 people. Your captain, including Holly, Amanda, Wallens, or Bryan, shapes the route around snorkeling, beaches, turtles, and island bars. Snorkel gear, water, soda, beer, park fees, and mooring permits are included, while fuel and gratuity cost extra.

“My family of 4 had an amazing day on the Poseidon with Captain Wallins. The boat was bigger than we needed, but it was so nice to not be on a ride with 30+ people. Wallins was so easy to get along with, knowledgeable and made my family feel very safe. We wanted to snorkel and he knew exactly what we would see at each stop (sea turtles, star fish, stingray, tropical fish, sunken sail boat, etc). Would definitely recommend to any of our friends.”

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St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin - The morning crossing and breakfast
British Virgin Islands Day Trips, Private Car and Van Tours, Sailing, Snorkeling, Tour Reviews, Tours in St John

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

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

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

Sail from the Westin St. John to Jost Van Dyke aboard a catamaran for an 8-hour day with a light breakfast, morning snorkeling, White Bay beach time, and an open bar on the return. Crews including Jolene, Riley, Eric, Brent, Dan, and Brendan handle customs and keep the day moving.

“Great tour and crew! They took us to a great snorkeling spot provided a great breakfast and drinks all day very a ton of crew and great experience”

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Day Yacht Excursions throughout the US or British Virgin Islands - Norman Island and its snorkeling caves
British Virgin Islands Day Trips, Sailing, Tour Reviews, Tours, Tours in St Thomas

Day Yacht Excursions throughout the US or British Virgin Islands

15.Day Yacht Excursions throughout the US or British Virgin Islands

★★★★★★★★★★5.0 · 164 reviews

Set out from Compass Point Marina aboard a private 45-foot yacht for 6 to 8 hours. Choose your route through the US or British Virgin Islands, from Norman Island’s snorkeling caves to Sandy Cay’s beaches. Hotel pickup is included, and meals, provisions, and fuel can be added depending on your package.

“Great Snorkeling and great sightseeing. Caring crew with great hospitality and lots of fun adventures”

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New in Sailing

★ 5.0Christmas Cove and Pizza Pi Happy Hour Sail TourFrom $18525 reviews
★ 5.0Norman Island – The Indians & The Caves Sailing & Snorkel TourFrom $19837 reviews
★ 5.0St. Thomas Sunset Sail, Serenity at SeaFrom $8941 reviews
★ 5.0St. John Luxury Catamaran Turtle Snorkel and Cays Full DayFrom $25035 reviews
★ 5.0St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast – Ritz-CarltonFrom $31937 reviews
★ 4.5Days End Sunset Sail Open Bar & Hors D’oeuvres STT Ritz-CarltonFrom $12945 reviews
★ 4.5St. Thomas Dinner Sail to St. John with Open Bar & Hors D’oeuvres – Ritz-CarltonFrom $14947 reviews
★ 5.0Full-Day Sailing Tour in Virgin Islands National ParkFrom $28544 reviews
★ 4.5St. John Sail with Bar and Hors d’Oeuvres to Lovango DinnerFrom $11935 reviews
★ 5.0St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)80 reviews
★ 5.0St. Thomas Maho Bay Turtle Snorkel Sail – Ritz-CarltonFrom $17953 reviews
★ 5.0Luxury Catamaran Champagne Sunset CruiseFrom $11980 reviews
★ 5.0Sail Away on your Private 55-foot Catamaran CharterFrom $1,89568 reviews
★ 5.0All-Inclusive Sunset Sail – Semi Private – Only 6 GuestsFrom $12990 reviews
★ 5.0Private Luxury Power Catamaran. Enjoy USVI Aboard MV Hydra52 reviews

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Sunset Sails14All-Inclusive Day Sails8Boat Charters18Cruises & Boat Tours16Island Hopping7British Virgin Islands Day Trips14
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