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All listings in the U.S. Virgin Islands

Awesome sailboat rentals in U.S. Virgin Islands.

Page 1 of 118 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

4.9
$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
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
$220/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
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

5.0
$2,000/day
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
All inclusive sailing charters, half day full day fishing week long sunset sail
Sailing in Charlotte Amalie · 12 guests

All inclusive sailing charters, half day full day fishing week long sunset sail

5.0
$250/hour
Instant Book
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
$1,300/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
Step into a world of refined elegance aboard Fountaine Pajot Alegria 67
Sailing in West End, Tortola · 8 guests

Step into a world of refined elegance aboard Fountaine Pajot Alegria 67

New
$10,000/night
Luxury Sailing Catamaran for up to10 guests
Sailing in St. Thomas · 12 guests

Luxury Sailing Catamaran for up to10 guests

New
$1,500/night
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
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250/hour
Luxury Sailing Catamaran for up to 12
Sailing in Cruz Bay · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
Snoozed - Active 18 Mar 2026

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Sailing Reviews in U.S. Virgin Islands

  1. CW

    Catherine

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

    Carrie was fantastic to work with when booking for our group. There were a lot of questions and some adjustments, and she was so kind a patient while answering everything! She even gave us a heads up the day of that there were storms coming so they might've not seen the sunset, and they were able to reschedule for the next day. Nothing but great things to say for the whole experience!

  2. SS

    Simon

    Luxury Sailing Catamaran for up to 12

    Unforgettable Post-Wedding Sail!! We spent a half-day with Aaron on the Catamaran Quest right after our wedding in St. Thomas, and it was easily one of the highlights of our entire trip. From the moment we stepped on board, Aaron made us feel incredibly special. He was super attentive and helpful, ensuring we had everything we needed to just relax and soak in the "just married" bliss. The food and drinks he served were fantastic—well-prepared and exactly what we needed for a day on the water. The boat itself is awesome and very well-equipped with everything you’d want for a comfortable excursion. We did encounter some minor technical issues with the engines during our trip, but Aaron handled it with total professionalism and didn't let it dampen the experience at all. If you are looking for a captain who truly cares about his guests' experience, book with Aaron. Thank you for making our celebration so memorable! PS: Aaron’s mango salsa is to die for - awesome stuff!!

  3. DG

    Davy

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

    The trip was great! Christian and Nicole were our captain. and they are the sweetest. They brought us to the best spots where we saw Turtles, stingrays, and even an eagle ray! The spot for lunch was amazing! They were so patient with our whole family, would highly recommend this trip we wish we could do this everyday.

  4. ek

    elizabeth

    Luxury Sailing Catamaran for up to 12

    Our family of 5 had an amazing day with Aaron! He had great communication leading up to our day. Everything about the day was great! He made us feel very at home on his beautiful boat and our day was so much fun! He was a great host!

  5. KD

    Kevin

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    Such a sweet couple and wonderful Mediterranean cuisine! A splendid way to end a week in paradise, not enough superlatives AND an opportunity To sail on an Oyster… WOOHOO!

  6. 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!!!