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All listings in the U.S. Virgin Islands

Awesome sailboat rentals in U.S. Virgin Islands.

Page 1 of 121 listings

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
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
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
$200+/hour
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
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. John pick up
Sailing in Cruz Bay · 6 guests

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

New
$350/hour
Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
Sailing in Freshwater Pond · 6 guests

Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

New
$3,666/night
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
 46' Oyster Sailboat in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

46' Oyster Sailboat in St. Thomas, Virgin Islands

5.0
Snoozed - Active 18 Jul 2025
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
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
Snoozed - Active 18 Jul 2025
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
Snoozed - Active 02 Apr 2026

Sailing Reviews in U.S. Virgin Islands

  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. RS

    Rob

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

    Captain Rachel and Nicolas made our trip great. They were both eager to help, offer suggestions, and just all around fun. We had a large group and were concerned about the size, but it was no problem. Ask for Captain Rachel & Nicolas and you won't be disappointed. Thanks for a great day.

  4. CM

    Candice

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

    My boyfriend and I booked a full day charter beginning and ending in St. Thomas as a part of a birthday celebration. The boat was perfect for a relaxing sail and we were able to select our own playlist while onboard. We had more than enough space for 2 people and would suggest this boat for up to 3 couples or a small group of friends. Rachel and Nick were excellent hosts - they were both warm and welcoming, shared interesting information about the islands, and made sure that safety was a top priority. We had a St. John beach location in mind and they suggested a complimentary lunch at Lovango, and the perfect spots to snorkel. Would definitely request these two if booking a trip!

  5. Alyice

    Alyice

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

    I really enjoyed my time with captain Rachel and Osay they where vary nice showed us a lot about the island..... they made sure we didn’t want for anything.... I give this boat a A+ I will definitely be renting this boat next time I come back to the island thank you making this the best part of my trip

  6. BC

    Brian

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

    Lovely half day exploring the USVI's - the boat was great and spacious, and the crew charted an efficient course to see as much as possible, while also fitting in water activity/snorkeling. The crew was kind, professional, and incredibly accommodating, highly recommend!