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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
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 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
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
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
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
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
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
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
Snoozed - Active 02 Apr 2026

Top Destinations Nearby

Sailing Reviews in St. Thomas

  1. Lisa

    Lisa

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

    We were a group of 13 and rented two catamaran’s for the afternoon. Captain JW was the captain for the boat I was on and he was terrific- took us to Scott beach on St. John for snorkeling and swimming. It was very pretty and he was very attentive in providing drinks and snorkeling equipment and good music. We sailed in tandem with the other catamaran that had the rest of our group on it and also went to a beautiful private resort called Lovango for lunch. Felt like a little taste of Europe in the US Virgin Islands. Only complaint was I wish we had even more time at sea but we had to get back on our cruise ship!

  2. MG

    Melanie

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    Shana and Nick were the best captains! Served lunch and delicious cocktails! Snorkeling and a relaxing sail. Perfect day!

  3. 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!!!

  4. 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.

  5. 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.

  6. 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!!