Virgin Islands · SAILING TRIPS IN ST THOMAS

The 15 Best Sailing Trips from St Thomas

47 tours  ·  from $89

Catamarans, monohulls and a few six-guest boats leave the south-coast marinas every morning. The 15 below compare them on price, guest count, lunch and how far out of the harbour they actually get.

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - The trip to Little Buck Island
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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
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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
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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
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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
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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
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Sunset Sail with Cocktails and Appetizers

7.Sunset Sail with Cocktails and Appetizers

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

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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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

9.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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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

10.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
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Private Fast Power Catamaran. Full or Half Day for Beach Hopping, Snorkel & Swim

11.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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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

12.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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Private Full Day, Fun Day Aboard SY Mazu - Luxury Gemini Legacy Catamaran - Starting in Red Hook at 9 a.m.
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Private Full Day, Fun Day Aboard SY Mazu – Luxury Gemini Legacy Catamaran

13.Private Full Day, Fun Day Aboard SY Mazu – Luxury Gemini Legacy Catamaran

★★★★★★★★★★5.0 · 153 reviews

Spend about seven hours aboard SY Mazu or SY Neptune with up to eight people, a captain, and crew member. Start in Red Hook, choose stops around St. Thomas and St. John, snorkel from the boat, visit beaches and Lovango Cay, and enjoy water, beer, soda, and rum punch. Confirm Cruz Bay pickup in advance.

“While there wasnt a whole lot of communication with this outfit prior to the trip, the trip went well. The crew was very good at servicing needs, educating us a little on the area and otherwise just very nice and very helpful. The boat was in good repair and clean. They took us to a couple of locations for snorkling and took us to a nice lunch spot. If you want a pretty easy day on a sailboat in the USVI with a good crew I can recommend this outfit. The only thing I wished is that it was a little easier to get in touch with them prior to…”

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Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar) - Breakfast, mimosas, and the crossing to Jost Van Dyke
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Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

14.Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

★★★★★★★★★★5.0 · 139 reviews · from $375

Set sail from Red Hook with a small group of up to 12 passengers, enjoying breakfast, bottomless mimosas, snorkeling gear, and an open boat bar. Stop at Foxy’s in Great Harbour, then spend three hours at White Bay and Soggy Dollar Bar. A passport and $85 cash customs fee are required.

“This trip was amazing! Awesome crew with outstanding service, small group, and beautiful scenery. The crew also gave us lots of local knowledge during the trip. Well worth the price. You will definitely have a fun day!”

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Full Day Sail with Max Charters - A six-person boat changes the whole day
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Full Day Sail with Max Charters

15.Full Day Sail with Max Charters

★★★★★★★★★★5.0 · 124 reviews · from $285

Join Max Charters from American Yacht Harbor for a six-hour sail around St. Thomas and nearby islands. With no more than six people aboard, you get guided snorkeling, secluded stops, a Mediterranean lunch, snacks, and a full bar. Cruise timing can be adjusted, making this a useful choice for ship passengers.

“We had the pleasure of snorkeling some of the best private dive sites with the crew. I’m a scuba diver with over 400 dives on sites the world over and these shallow reefs we visited were some of the best shallow dives I’ve ever experiencRead more”

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New in Sailing Trips in St Thomas

★ 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
★ 5.0Sail and Snorkel Private Charter – Half Day MorningFrom $1696 reviews
★ 4.5Full or Half Day Private Power Catamaran- USVI Beach and Snorkel34 reviews
★ 4.5Sail, Shop and Snorkel in St. John from Frenchman’s ReefFrom $12918 reviews
★ 5.0Private Full Day Sail/ Snorkel Experience USVI (Sapphire Marina, STT pick up)16 reviews

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