We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in the U.S. Virgin Islands

Awesome sailboat rentals in U.S. Virgin Islands.

Page 1 of 124 listings

Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran
Events in St. Thomas · 12 guests

Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran

5.0
$350hour
 46' Oyster Sailboat in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

46' Oyster Sailboat in St. Thomas, Virgin Islands

5.0
$485day
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
$1,550day
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
$390hour
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
$210hour
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
$293hour
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$485day
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
$220hour
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
$365hour
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
$2,395day
Best Value - Full Day Private Charter Aboard MV Sea Wolf -Holiday Rate Reduced
Events in St. Thomas · 12 guests

Best Value - Full Day Private Charter Aboard MV Sea Wolf -Holiday Rate Reduced

5.0
$1,795day
46' Monohull Sailing Private Charter in Charlotte Amalie
Sailing in St. Thomas · 6 guests

46' Monohull Sailing Private Charter in Charlotte Amalie

New
$200hour
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
$125hour
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250hour
Dive Tours and Snorkeling With The Turtles
Tours in St. Thomas · 40 guests

Dive Tours and Snorkeling With The Turtles

New
$125person
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
$325hour
Ad Astra Luxury Catamaran Day Sail in Freshwater Pond, Tortola
Sailing in West End, Tortola · 12 guests

Ad Astra Luxury Catamaran Day Sail in Freshwater Pond, Tortola

New
$1,950day
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
$325hour
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
$2,000day
Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands with with Captain Rick!
Sailing in Cruz Bay · 12 guests

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

New
$1,000day
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 10 guests

Sailing catamaran in USVI

New
$1,300day
St John, usvi  private day  sail excursions
Sailing in Charlotte Amalie West · 6 guests

St John, usvi private day sail excursions

New
$175person
Beautiful days with your friends and family on a Brand New Elba 45’ in St. Thomas and St. John, USVI.
Sailing in Charlotte Amalie West · 6 guests

Beautiful days with your friends and family on a Brand New Elba 45’ in St. Thomas and St. John, USVI.

New
$1,715day
72 ft Cruising Monohull Charter for 4 Peopl in St. Thomas, US Virgin Islands
Sailing in St. Thomas · 4 guests

72 ft Cruising Monohull Charter for 4 Peopl in St. Thomas, US Virgin Islands

New
$2,143day

Sailing Reviews in U.S. Virgin Islands

  1. 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.

  2. RP

    Ritchie

    Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran

    Laurie’s staff, Ian and Sara were phenomenal!! This was our first time to St .Thomas and we had no idea where to go. They offered up an itinerary in place for us to maximize the fun and sight seeing. Extremely helpful and the boat itself was a thing of beauty!! More than enough space for the 8 of us not including the 2 crew staff. Would highly recommend booking with Laurie if you’re looking for a really nice boat and want to be treated like a rockstar!!!

  3. 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!

  4. Jubril

    Jubril

    Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran

    Laurie, your team is fantastic. I had a great time and boat (Cat) is great beautiful and well maintained. We went ST John’s and snorkeled such beautiful waters. I appreciated the snacks and everything as well. Service was truly A1. Thank you again

  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!!