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All listings in St. Thomas

Incredible sailboat rentals in St. Thomas, U.S. Virgin Islands.

Page 1 of 120 listings

 46' Oyster Sailboat in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

46' Oyster Sailboat in St. Thomas, Virgin Islands

5.0
$197+/hour
Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing
Sailing in St. Thomas · 12 guests

Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing

5.0
$1,550/day
Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

4.8
$390/hour
Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI
Sailing in Charlotte Amalie · 12 guests

Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

5.0
$293/hour
Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands
Sailing in Charlotte Amalie West · 6 guests

Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

5.0
$210/hour
Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran
Sailing in Charlotte Amalie · 12 guests

Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

4.6
$365/hour
Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!
Sailing in St. Thomas · 10 guests

Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

5.0
$225/hour
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

5.0
$2,395/day
46' Monohull Sailing Private Charter in Charlotte Amalie
Sailing in St. Thomas · 6 guests

46' Monohull Sailing Private Charter in Charlotte Amalie

New
$200/hour
Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick
Sailing in Cruz Bay · 12 guests

Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

5.0
$125/hour
Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up
Sailing in Cruz Bay · 6 guests

Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up

New
$350/hour
Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. Thomas pick up
Sailing in Charlotte Amalie · 6 guests

Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. Thomas pick up

New
$350/hour
45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands
Sailing in St. Thomas · 12 guests

45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

New
$2,000/day
Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands!
Sailing in Cruz Bay · 12 guests

Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands!

New
$1,200/day
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 10 guests

Sailing catamaran in USVI

New
$1,300/day
Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI
Sailing in Charlotte Amalie West · 6 guests

Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI

New
$250/hour
Instant Book
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
Snoozed - Active 23 Jan 2026
A Large, Comfortable and Spacious Luxury Sailing Yacht for 12 in St Thomas/STJ
Sailing in St. Thomas · 12 guests

A Large, Comfortable and Spacious Luxury Sailing Yacht for 12 in St Thomas/STJ

5.0
Snoozed - Active 30 Nov 2025

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Sailing Reviews in St. Thomas

  1. Mariella

    Mariella

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    BOOK NOW! this sail was one of the greatest experiences we have had on the water. The boat was beautiful, comfortable, and sailed like a dream. The food was DELICIOUS! The drinks - amazing! The service was unmatched. Shana and Nicholas made sure to make our day we so special. We found some great snorkeling spots, enjoyed a sail around the islands, and a gorgeous sunset. We feel blessed to have been a part of their sail today - we will be back!! Communication 10/10. On time 10/10. Kind and great hosts 10/10!!!

  2. Suzanne

    Suzanne

    Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

    We chartered Saltwater Taffy whilst on a recent cruise to St Thomas. The 4 of us had the best time ever. Great communication from Rosie on the days before the sailing. We were met at the ship by Brad and driven to the boat where we met Rosie and Bosun the cat. We set sail straight away into turquoise waters and we were quickly under sail. We chose to snorkel with turtles so we went to Scott beach, got kitted up with snorkels and Brad took us to the beach in the motor rib. It’s really easy to get in and out of the water from the swim platform. We swam for about 10 minutes until we found the turtles. They are just so graceful. Brad got some great underwater pics. We then went back to the boat where Rosie had been preparing an amazing lunch and cocktails. We then motored back to the dock. Best day ever and we will be back to do it all over again. Thanks so much. Suzanne, Chris, Pam and Ricky xxxx

  3. DH

    Denise

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    Our sailing excursion was wonderful! Shana was excellent with communication ensuring we knew exactly where to meet for the excursion and that we were back in time to catch our ship. The sailing was beautiful and relaxing! Snorkeling at St James was fantastic and the food was delicious. We would highly recommend booking your sailing excursion with them.

  4. Thomas

    Thomas

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    I can’t recommend this charter enough. Everything was get. Shana and Nicholas are fantastic hosts. They took us to great snorkeling spots, a beach that we had all to ourselves, the food was excellent and we never had an empty drink. They were also just a lot of fun to talk to. Everyone in our group was very happy. I didn’t want it to end.

  5. JR

    JAMIE

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    I wanted a real sailing experience as well as going to different beaches around the Virgin Islands and I got that and so much more , the vessel isn’t some coastal water princess it’s a sea queen , the food and service was more than I could ask for . Shana and her family were inviting and kind . Long story short I will stay in contact and seek them out anytime I want this awesome experience again!!

  6. Karin

    Karin

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    Shana, Nick and Jaye, best crew ever! We had a wonderful day, visited beautiful honeymoon beach in St John and other islands where we snorkeled. Food and drink were fantastic. Didn’t spare in anything, only wanted us to have a great time. FfDefinitely will choose them again!