Top St Thomas Sailing Tours

Half Day Sail and Snorkel with the Turtles

3 hours 30 minutesFree Cancellation

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

(306)

from $149

(253)

from $159

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select a half or full day charter. Visit the islands of St. Thomas, St. John and surrounding cays. SY Sirena is a 50′ Luxury catamaran with a spacious salon that opens on to an expansive back deck with seating and dining. The bow of the boat offers relaxing seating with bean bag chairs and large trampolines for group conversations, tanning or intense turtle, dolphin watching. There are plenty of water toys to keep you entertained, from snorkeling equipment to relaxing floats. Price includes ice, soda, beer and rum punch. You and our captain will design an itinerary that best meets the needs of your group. *Please note the BVI is not available on this vessel, but a visit to the BVI can be booked under Product Codes 111649P24 or 111649P25. Departure from American Yacht Harbor in Red Hook; pickup from Cruz Bay, STJ possible with advance request after booking.

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

4 to 7 hoursFree Cancellation

(672)

from $1,595

Set sail on St Thomas' aquamarine waters during this 3-hour sailing excursion from Frenchman's Cove. Step aboard the 54-foot (16-meter) catamaran and meet your friendly captain and crew. Head for the serene waters of Little Buck Island National Wildlife Refuge, where you'll don the provided snorkeling gear and jump in to snorkel among the vibrant marine life. Snacks, pirate tattoos and unlimited drinks from the open bar are included.

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Half Day Private Sailing Catamaran and Snorkel Trip to St John

(2,257)

from $119

3 hours 30 minutesFree Cancellation

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

(103)

from $165

6 hours 30 minutesFree Cancellation

(690)

from $245

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half or full day charter. Visit the islands and harbors of St. Thomas, Buck Island, Water Island, and maybe even a secret cay! S/Y Pisces is a 47′ luxury Leopard Catamaran with a spacious salon that opens on to an expansive back deck with comfortable seating. The bow of the boat offers relaxing seating with bean bag chairs and two large trampolines for group conversations, breezy tanning or turtle watching. Equipped with the latest in audio technology, Pisces has a JBL sound system with Bluetooth capability to ensure you travel with your favorite tunes. There are plenty of water toys to keep you entertained, from snorkeling equipment and relaxing floats to beach games. You and our captain will design an itinerary that best meets your needs. All departure times are listed in Local Island Time.

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

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

7 hoursFree Cancellation

(412)

from $1,495

Snorkel Cat All Inclusive Adventure

5 hoursFree Cancellation

Sail, Shop and Snorkel in St. John from Westin Frenchman's Reef

(957)

from $150

(26)

from $129

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This trip is limited to only 12 guests. Start the morning with Muffins Fruit and a full open bar w/bottomless mimosa's are served as we sail along the beautiful Northern Cays of the USVI. We check into the BVI Customs and you will receive a new stamp in your passport. You'll get to explore the town of Great Harbor with its sandy Main Street and maybe even meet Foxy himself while you get to enjoy some Fire Water Rum or grab a souvenir at the boutique. After Great Harbor we sail over to the beautiful White Bay, which is home to The Soggy Dollar Bar to spend the entire afternoon. This 9 hour trip will give the maximum time at White Bay and The Soggy Dollar Bar. ** This is an International Excursion and a Valid Passport and USD85 cash customs fees per person is required ** This is a share trip with other guests. This is NOT a private tour

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

8 hours

(175)

from $395

All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

2 hoursFree Cancellation

St. Thomas Maho Bay Turtle Snorkel Sail - Ritz-Carlton

(105)

from $139

5 hoursFree Cancellation

Full Day Sail with Max Charters

(59)

from $199

(133)

from $285

Luxury Private Sunset Cruise for up to 6 guests

2 hoursFree Cancellation

(37)

from $695

St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton

5 hoursFree Cancellation

4.6

(56)

from $149

St. Thomas Dinner Sail to Lovango w/ Open Bar and Hors D'oeuvres

Treat yourself to a dinnertime sailing trip aboard a luxury 65-foot-long catamaran, Lady Lynsey II. You'll sail from the Ritz-Carlton out to the Lovango Resort and Beach Club (situated on a private island), with hors d'oeuvres and cocktails served along the way. Once you arrive at the club, you'll sit down to a meal of fresh seafood and more cocktails, followed by dessert on your return cruise home.

St. Thomas Dinner Sail to Lovango w/ Open Bar and Hors D'oeuvres

4 hoursFree Cancellation

4.6

(44)

from $139

Full-Day Sailing Tour in Virgin Islands National Park

(49)

from $285

Days End Sunset Sail Open Bar & Hors D'oeuvres STT Ritz-Carlton

1 hour 30 minutesFree Cancellation

4.6

(51)

from $149

I Like Turtles Private Sailing and Snorkeling from Sapphire

(3)

from $799

Be sure to come hungry for this dinner cruise that’s strategically timed so you enjoy the Charlotte Amalie harbor lights and sunset. Get comfortable aboard the 54-foot (16-meter) catamaran as you sail through the harbor, sipping a drink from the open bar. Dinner includes options for all preferences, including tacos on Tuesdays and barbecue on Wednesdays, Fridays, and Saturdays. Dietary restrictions can be accommodated with advance notice.

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

2 hoursFree Cancellation

Simply Sailing Private Sail from Sapphire Marina

(1,271)

from $119

(19)

from $799

Private Full Day Sail in Virgin Islands National Park

(17)

from $1,650

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

8 hoursFree Cancellation

Half Day Private Sailing Catamaran and Snorkel Trip to St John

(49)

from $319

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What are people saying about St Thomas

Erin_W, May 2026

Wishing for more time

The catamaran was a perfect size for our party, there were 6 of us total, not including the captain and his mate. The advertisement is described as a “half day” snorkel tour to St. John, which amounted to 3.5 hrs. I will say I wish this had been longer. It took 1 hour to sail to St. John from St. Thomas and 1 hour to sail back. So essentially we only had 1 hour to Snorkel, which isn’t alot of time. I think the charter itself could have been at least 5 hours. We left at 10:30am and were back by 2pm. All in all the excursion was great, Ryan and his crew member were very nice and very informative about the islands and surrounding areas as we sailed. We 100% recommend this experience to anyone who wants a day out on the water.

Half Day Sail and Snorkel with the Turtles

Gona_M, May 2026

Wonderful Excursion

Captain Mike & his shipmate Vanessa are very knowledgeable of sailing. They explain everything in detail & make you feel safe. My sister & I spent my 60th on this excursion. There were only 5 other people on the boat & this made for a more personalized trip. They explained how to use the snorkel & mask, sanitized each one, helped you get in & out of the water, if you needed help. You had options to use a life vest or not, a noddle if you preferred, a floating mask if you were not comfortable with a snorkel & mask. We went from the Marina to Buck island & they told some history of the area & answered our questions. Vanessa got into the water with us & showed us where to go see the turtles. She brought up a large shell with a crab in it & let each person hold it & take pics. We saw several turtles, a lot of fish & we snorkeled over beautiful coral where there were small & large sea urchins. I saw a small octopus. Great music, light refreshments & Rum punch on your way back to the Marina. Don’t miss out on a wonderful experience to sail & snorkel with sea Turtles & so much more. The only regret was forgetting my waterproof phone pouch but a nice lady (Callie) sent me some underwear pics. 🙂

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

Clara_V, May 2026

Relaxing sailing...

Relaxing sailing experience with personal attention. The small group size made it especially enjoyable. Captain Kendall was very knowledgeable, attentive and competent. He took us to some very special snorkeling spots and had a thorough knowledge of the area. I would highly recommend this trip.

St Thomas Shore Excursion: Mangrove Lagoon Kayak and Snorkel Tour

Justine_J, Apr 2026

Had a great experience...

Had a great experience even with some confusion on the pickup area and staff shortage. Staff truly over delivered and made what could have been a miserable experience into something we’ll never forget. Office staff is responsive and was quick to solve issues/flexible on a solution. The guide staff was passionate about nature and local wildlife. Shout out to our guide Primo :) and don’t forget the sunblock!

Days End Sunset Sail Open Bar & Hors D'oeuvres STT Ritz-Carlton

Amelia_H, Apr 2026

Does not board from a dock

Crew was welcoming and the bar was open as soon as we boarded until we returned. Food was good and sunset beautiful. You should know you have walk through sang, remove shoes and walk through water to board. It is slippery and impossible to see upon return. Shoes are kept for duration of the sail and retuned on the beach. We had fun but that was unexpected. We also set a dinner reservation at the hotel for 7:30 and made it in plenty of time.

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

Madelyn_B, Apr 2026

This was so fun! My...

This was so fun! My husband wasn’t feeling well at one point but Rob and Deb took amazing care of him. Made sure he had water at all times, also made sure everyone on the boat had what they needed. The hospitality was unmatched! Deb constantly filled our cups up with whatever drink we wanted, she offered us snacks after snorkeling too! Rob gave us some good dinner recs and told us some good info about the island. We would definitely recommend this to anyone!

St. Thomas Maho Bay Turtle Snorkel Sail - Ritz-Carlton

Bill_C, Apr 2026

Outstanding Snorkel Sail Experience – Highly Recommend Captain Jolene & Crew

Our Turtle Snorkel Sail to Maho Bay out of St. Thomas was truly unforgettable, and Captain Jolene and her exceptional crew made it a five‑star experience from start to finish. From the moment we stepped aboard, we were welcomed with genuine warmth, professionalism, and attention to detail that perfectly matched the Ritz‑Carlton standard. Captain Jolene was knowledgeable, calm, and engaging, making everyone feel comfortable and cared for throughout the sail. Her crew was equally impressive—friendly, attentive, and always ready to help, whether it was assisting with gear, sharing insights about the area, or making sure everyone had exactly what they needed. Maho Bay was spectacular, and snorkeling with sea turtles in such clear, beautiful water was a highlight of our trip. The crew took great care to ensure the experience was safe, relaxed, and enjoyable for guests of all experience levels. If you’re looking for a seamless, memorable snorkeling adventure with top‑tier service, I can’t recommend Captain Jolene and her crew enough. This was hands‑down one of the best experiences of our time in St. Thomas and a must‑do for anyone staying in St Thomas

St. Thomas Dinner Sail to St. John with Open Bar & Hors D'oeuvres - Ritz-Carlton

Linda_A, Feb 2026

Nice relaxing trip to and...

Nice relaxing trip to and from St John from St Thomas. The crew was super attentive and helped navigate of recommended spots once I got to St John. They even walked everyone to their dinner reservations locations. Loved a smaller group vs the normal 80.

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

Robin_H, Feb 2026

Great day to Jost Van Dyke

We had a wonderful day on our Stormy Pirates boat trip to JVD. Kenny and Suzanne were so nice and solicitous of our every need. Boat was very clean, check in was a breeze, nice food nibbles for breakfast and cookies in the afternoon! Everything you could want to drink throughout the day. Just a lovely day on the water. Highly recommend.

All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

Maureen_T, Jan 2026

Enjoyable Sunset Cruise

Captain Kendall is experienced, engaging and knowledgeable about the local area, and ably manages the cruise as captain, bartender and crew. Drinks were good. Boat seats 6 comfortably. No need to arrive to board early as removing shoes and boarding process is quick and easy. We had a delightful time.

Days End Sunset Sail from the Westin at Frenchman's Reef

DKimberly_M, Nov 2025

Smooth sailing

While the clouds interrupted the sunset, it was still a beautiful night and colorful sky behind the clouds. Great crew who were attentive, friendly, and knowledgeable. One person in the party is susceptible to motion sickness, and they had no problems on the main deck. Highly recommend!

Full-Day Sailing Tour in Virgin Islands National Park

Trish_S, Jul 2025

A Fun and Relaxing Sailing Excursion!

We had a wonderful sailing, snorkeling experience! Captain Kendall and Casey are experts in sailing and hosting. Attention to both safety and having a memorable day! Plenty of drinks and snacks of all kinds, including A charcuterie board of crackers, cheese and fresh fruit. Lunch was delicious; chicken grilled by the captain while Casey guided a group of us snorkeling. Their knowledge of the area was impressive even to the exact location of the ocean home of a weathered pufferfish. While snorkeling we saw colorful fish, sting rays, turtles and an octopus! Underwater terrain itself was fascinating. Captain Kendall and Casey were very knowledgeable about the islands and their histories, freely conversing and answering questions throughout our journey! Highly recommend!!!