Virgin Islands · SAILING

The 15 Best Sailing Trips in the Virgin Islands

64 tours  ·  from $55

Sir Francis Drake Channel is sheltered water with steady trade winds, which is why the charter fleet lives here. These 15 sailing days range from a half-day snorkel run to a full crossing into British waters, priced and clear about how much is under sail.

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - The trip to Little Buck Island
Cruises & Boat Tours, Sailing, Sailing Trips in St Thomas, Sea Turtle Snorkeling, Snorkeling, Snorkeling Tours in St Thomas, St Thomas Tours, Tour Reviews

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

Sail The VI Cat from Marriott Frenchman’s Cove to Little Buck Island with Captain Serena, Tim, Anders, Isaac, Nick, or Porscha guiding the day. You get snorkel gear, about an hour in the water, sea turtles, reef fish, snacks, and drinks after swimming. The 1 p.m. departure can feel calmer than cruise-ship morning trips.

“Amazing tour with approx. one hour of snorkeling with an amazing crew. My family really enjoyed the boat and the views. When we went snorkeling, the crew made sure that we were safe and knew everything before we got into the water. ThRead more”

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Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - The VI Cat gives you room to roam
Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Sailing, Sailing Trips in St Thomas, St Thomas Tours, Sunset Cruises, Tour Reviews

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. You will enjoy an open bar, scratch-made tacos or barbecue, music, and views toward Little Buck Island and Charlotte Amalie. The crew, including Captain Dave, Mike, Isaac, Anders, and Adrian on some departures, keeps the evening social and relaxed.

“It’s fun, good food, friendly staff, prompt and generous drinks. Great time of day and just long enough.”

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Champagne Sunset Sail from Margaritaville - What the open bar really adds
Cruises & Boat Tours, Evening Experiences, Sailing, Sailing Trips in St Thomas, St Thomas Tours, Sunset Cruises, Tour Reviews

Champagne Sunset Sail from Margaritaville

3.Champagne Sunset Sail from Margaritaville

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

Sail from Margaritaville on a new catamaran for about two hours, with Champagne, wine, cocktails, Painkillers, rum punch, soft drinks, and hors d’oeuvres included. The crew may include captains such as Big Tuna, Danny Boy, or Sean, with sunset and moonrise views around St. Thomas. Expect a social, barefoot boat outing for up to 70 people.

“Captain and crew were excellent. Food was delicious and the drinks were great. It was a rainy evening and the captain found clear skies for us to enjoy our sail.”

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St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max - Two or three snorkel stops, not one rushed swim
Cruises & Boat Tours, Full-Day, Sailing, Sailing Trips in St Thomas, Snorkeling, Snorkeling Tours in St Thomas, St Thomas Tours, Tour Reviews

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

Spend about six and a half hours aboard a small sailboat with a maximum of six people. From Sapphire Beach Marina, Captain Kendall, Addison, Tommy, Mark, Rusty, Sam, or Gabi may guide you toward St. John National Park and nearby cays. Expect two or three snorkel stops, lunch, drinks, and a flexible route shaped by weather and crowds.

“Mark and Rusty made the day so fun! It was a windy day, which made for a “sporty” journey. We got to snorkel at three wonderful locations, where we saw turtles, lobsters, rays, and fish of many stripes and colors. The food was delicious and the drinks were plentiful. Excellent service!”

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Half Day Luxury Catamaran Turtle Snorkel And Beach - Leaving Yacht Haven Grande for the southern coast
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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 aboard Someday Charters’ modern catamaran for four hours along St. Thomas’ southern coast. Snorkel at Turtle Cove near Buck Island, look for green sea turtles and reef fish, then relax at Honeymoon Beach. The trip includes gear, snacks, fresh-water rinse, and an open bar after swimming.

“Excellent experience and customer service all the way around! Wonderful snorkeling, catamaran ride and day.”

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50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience - The St. Thomas options: coves, beaches, and easy snorkeling
Cruises & Boat Tours, Private, Sailing, Sailing Trips in St Thomas, Snorkeling, Snorkeling Tours in St Thomas, St Thomas Tours, Tour Reviews, 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

Charter the 50-foot SY Sirena for four to seven hours with up to 12 people. Your captain sets the route around St. Thomas, St. John, and nearby cays, with snorkeling gear, floats, beer, soda, water, and rum punch included. Captains such as Maddy, JW, Alex, and Dave are praised for adapting the day to families, swimmers, and snorkelers.

“Coleman and Maddie were amazing. We snorkeled with turtles, did some sightseeing on the amazing catamaran then snorkeled the reef. Perfect afternoon. Unfortunately the next day we were scammed in St.Maarten with a trip through Viator. This one is real and amazing way to spend your time in St.Thomas”

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Sunset Sail with Cocktails and Appetizers - What the crew adds to the evening
Cruises & Boat Tours, Evening Experiences, Sailing, Sailing Trips in St Thomas, St Thomas Tours, Sunset Cruises, Tour Reviews

Sunset Sail with Cocktails and Appetizers

7.Sunset Sail with Cocktails and Appetizers

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

Sail around Charlotte Amalie Harbor aboard the 54-foot VI Cat from Marriott’s Frenchman’s Cove. Expect a relaxed sunset cruise, open bar, light snacks, music, and attentive crew such as Serena, Isaac, Nick, and Portia. The cruise lasts about two hours and returns to the dock in time for dinner.

“Great time, relaxing and the drinks never stop 😊 the staff was very friendly and made the trip very comfortable I would definitely recommend”

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Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. - Snorkeling with turtles, rays, and reef fish
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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

Spend a half or full day aboard S/Y Pisces, a private 47-foot Leopard catamaran for up to 12 people. With your captain, plan a route around St. Thomas, Water Island, Buck Island, and nearby coves. Snorkel, swim, relax on the trampolines, play your own music, and enjoy rum punch, beer, soda, and water.

“Exactly what we needed! We spent an amazing day with Annemarie and Selena relaxing, snorkeling, and swimming. Our experience couldn’t have been better!”

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Live Music Sunset Sail - The Music Sets the Pace
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Live Music Sunset Sail

9.Live Music Sunset Sail

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

Sail from Frederiksted Pier for roughly two hours on a catamaran with live local music, unlimited Cruzan rum punch for adults, and views of Frederiksted, Sandy Point National Wildlife Refuge, sea turtle tracks, and the setting sun. The crew may include Captain Mike, Chase, Bret, Taylor, or B, with musicians such as Pete appearing on some departures.

“Beautiful sunset sail around Fredericksted! Weather was great and sunset was lovely. Super nice and responsible crew as well. Highly recommend!”

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Half Day Sail and Snorkel with the Turtles - The ladder, equipment, and comfort level
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Half Day Sail and Snorkel with the Turtles

10.Half Day Sail and Snorkel with the Turtles

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

Sail from Charlotte Amalie aboard Fury with Captain Mike and Nikki, then snorkel in calm Turtle Cove near Buck Island. You’ll receive gear, a short water briefing, turtle-behavior commentary, snacks, drinks, and a freshwater rinse. The boat carries up to 25 people, though many departures are smaller.

“Awesome day saw few turtles and a barracuda. Capt Mike and Nikki are the best very knowledgeable of the area wonderful guides. Thank you for a great memories.”

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St. John Days End Sunset Sail Open Bar & Hors D'oeuvres - Westin - Champagne, cocktails, and small bites
Cruises & Boat Tours, Evening Experiences, Sailing, Sailing Trips in St John, St John Tours, Sunset Cruises, Tour Reviews

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

Sail with Captain Rob and Deb aboard Cosmos Mariner from Sapphire Beach Marina. This three-hour, six-person trip pairs real sailing with snorkeling near Caneel Bay, Christmas Cove, or Lovango, depending on weather. Gear, snacks, soft drinks, and alcohol are included. Expect a small boarding ladder and about an hour in the water.

“This was such an amazing experience Rob and Deb were such wonderful hosts. Incredibly knowledgeable and friendly. The rum punch was an added plus it was so delicious and the sailing part of our journey was so relaxing and unforgettably beautiful. We had an incredible time. We went to a cove thriving with coral, fish, sea turtles, and a shipwreck! We would love to book with them again. Thank you Deb & Rob for such a perfect adventure!”

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Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim - Boarding at American Yacht Harbor in Red Hook
Beach Tours, Beach Tours in St Thomas, Boat Charters, Cruises & Boat Tours, Private, Sailing, Sailing Trips in St Thomas, Snorkeling, Snorkeling Tours in St Thomas, St Thomas Tours, Tour Reviews

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

Take a private cruise from Red Hook aboard the 36-foot MV Poseidon, a fast, stable TwinVee catamaran for up to 12 people. Your captain shapes the route around snorkeling, beaches, swimming, or lunch stops. Water, soft drinks, beer, snorkel gear, park fees, and mooring permits are included, with fuel and tip extra.

“Such a wonderful experience! Wallens took us to two great spots. One with turtles and another with so many species of fish. We had a quick stop at a unique beach with amazing drinks and clean bathrooms. The music was on point for a chill experience. Such an epic and chill day. Thank you Wallens!”

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St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin - Morning snorkeling near coral reefs
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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

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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Day Yacht Excursions throughout the US or British Virgin Islands - Building a route through the Virgin Islands
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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

You’ll spend 6 to 8 hours aboard a private 45-foot yacht from Compass Point Marina, with room for up to 12 people. Build your own route through the US or British Virgin Islands, perhaps stopping at Norman Island caves or Sandy Cay beaches. Hotel pickup is included, while fuel, customs fees, and provisioning may cost extra.

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

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New in Sailing

★ 4.5Sailing and Snorkeling to Norman Island and Caves7 reviews
★ 5.0Soggy Dollar & Sandy Spit Sailing Tour in the BVIFrom $2089 reviews
★ 5.0Sandy Spit & Soggy Dollar Sailing Tour in the BVIFrom $22831 reviews
★ 5.0All Inclusive Day Sail to Soggy Dollar Bar, White Bay, JVD3 reviews
★ 4.0Turtle Snorkel Sail on Buck Island from Frenchman’s ReefFrom $1298 reviews
★ 5.0Sail and Snorkel Private Charter – Mid-Day Sail 1230pm to SunsetFrom $2196 reviews
★ 5.0Simply Sailing Private Sail from Sapphire Marina19 reviews
★ 5.0St. John Luxury Catamaran Turtle Snorkel and Cays Full DayFrom $25035 reviews
★ 5.0Private St Thomas Luxury Catamaran Trip for Groups up to 24 Guest6 reviews
★ 5.0Private Sunset Sail, Open Bar, 12 Guests, Amazing Island ViewsFrom $1,3454 reviews
★ 5.0Private Power Catamaran. Secluded Beaches, Snorkeling, Turtles for Full/Half Day12 reviews
★ 5.0Private Luxury Catamaran Champagne Sunset Cruise4 reviews
★ 5.0Private Luxury Catamaran Half Day Charter5 reviews
★ 5.0Private Full Day Sail in Virgin Islands National Park16 reviews
★ 5.0Christmas Cove and Pizza Pi Happy Hour Sail TourFrom $18525 reviews

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