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All listings in St. Thomas

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

4.9(Average of 100 reviews in this area)
24 listings
Book the 46' Oyster Center Cockpit Ketch Rigged Vessel in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

Book the 46' Oyster Center Cockpit Ketch Rigged Vessel in St. Thomas, Virgin Islands

5.0
$485day
Private Full Day, Fun Day Aboard SY Mazu - Luxury Gemini Legacy Catamaran
Sailing in St. Thomas · 12 guests

Private Full Day, Fun Day Aboard SY Mazu - Luxury Gemini Legacy Catamaran

5.0
$1,495day
Half Day 50' Private Sailing Catamaran. Luxury, Beach and Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

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

4.8
$298hour
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
$1,695day
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
$298hour
Sailing Cruises in St. John, U.S. Virgin Islands, Onboard Sailing Ketch Rigged Center Cockpit Oyster
Sailing in Cruz Bay · 6 guests

Sailing Cruises in St. John, U.S. Virgin Islands, Onboard Sailing Ketch Rigged Center Cockpit Oyster

5.0
$485day
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
$175person
Sail Away in St Thomas/St.John aboard a beautiful Catalina 42 Mkii Sailboat for 10 Guests
Sailing in St. Thomas · 6 guests

Sail Away in St Thomas/St.John aboard a beautiful Catalina 42 Mkii Sailboat for 10 Guests

5.0
$500day
Full Day 50' Private Sailing Catamaran. Luxury, Beach and Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

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

5.0
$1,995day
Best Value - Full Day Private Charter Aboard MV Sea Wolf NavalCat
Events in St. Thomas · 12 guests

Best Value - Full Day Private Charter Aboard MV Sea Wolf NavalCat

5.0
$1,595day
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
46' Monohull Sailing Private Charter in Charlotte Amalie
Sailing in St. Thomas · 6 guests

46' Monohull Sailing Private Charter in Charlotte Amalie

New
$200hour
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
$1,850day
Private Sailing Trip Aboard 46ft Leopard Luxury Catamaran in Charlotte Amalie, St. Thomas
Sailing in Charlotte Amalie · 6 guests

Private Sailing Trip Aboard 46ft Leopard Luxury Catamaran in Charlotte Amalie, St. Thomas

New
$262hour
Sailing Day Charter in St. John USVI on a Luxury 46ft Catamaran!
Sailing in Cruz Bay · 6 guests

Sailing Day Charter in St. John USVI on a Luxury 46ft Catamaran!

New
$262hour
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 10 guests

Sailing catamaran in USVI

New
$1,300day
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

New
$125hour
Day and Overnight Charters on our luxurious electric eco-catamaran
Sailing in St. Thomas · 12 guests

Day and Overnight Charters on our luxurious electric eco-catamaran

New
$1,600day
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
Day Sail Classic Restored Wood Yacht in Charlotte Amalie
Sailing in Charlotte Amalie · 6 guests

Day Sail Classic Restored Wood Yacht in Charlotte Amalie

New
$250hour
St John, usvi  private day  sail excursions
Sailing in Charlotte Amalie West · 6 guests

St John, usvi private day sail excursions

New
$175person
Captained Charter on 50' Sailing Yacht in Charlotte Amalie, USVI
Sailing in Charlotte Amalie · 4 guests

Captained Charter on 50' Sailing Yacht in Charlotte Amalie, USVI

New
$8,900week
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
$12,000week
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

Top Destinations Nearby

Sailing Reviews in St. Thomas

  1. TL
    Tanya L
    46' Monohull Sailing Private Charter in Charlotte Amalie

    Captain Fancy and Lindsey were awesome!! We loved every minute of it. Pedro the pirate dog was so sweet. I would post pictures but not sure how. I don’t see an option.

  2. JR
    JAMIE
    Book the 46' Oyster Center Cockpit Ketch Rigged Vessel 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!!

  3. Karin
    Karin
    Book the 46' Oyster Center Cockpit Ketch Rigged Vessel 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!

  4. NM
    Nicolas
    Book the 46' Oyster Center Cockpit Ketch Rigged Vessel in St. Thomas, Virgin Islands

    A must have experience for anybody wanting the full Virgin Islands immersion. Shana and Nicholas where fun and extremely knowledgeable, taking us to amazing spots to snorkel. The drinks and food where also to die for. I could not recommend more highly.

  5. ES
    Eric
    Book the 46' Oyster Center Cockpit Ketch Rigged Vessel in St. Thomas, Virgin Islands

    Shana and Nicolas's boat was absolutely wonderful. They are super hospitable host, getting the information from us on what we wanted to see they were able to make this an amazing memory for my wife and I on our honeymoon! The food was absolutely amazing and completely accommodating to a dairy-free diet. Great conversation and a wonderful excursion!

  6. vs
    vlad
    Book the 46' Oyster Center Cockpit Ketch Rigged Vessel in St. Thomas, Virgin Islands

    Shana and Nick (captain) were great!!.. everything was smooth from the pick up to the all day on the boat taking us around great snorkeling spots around St John and a few private beaches. Drinks and food was also a very nice touch. Overall a great sailing experience! Thanks!