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Hire a sailing boat in the Caribbean

Yacht
301 results
Hire Sailboat Dufour Yachts Dufour 412 GL Saint Thomas
Discount offer
6
· 
Saint Thomas

From 571 £ per day

Hire Sailboat JEANNEAU Sun Odyssey 519 with watermaker & A/C - PLUS Saint Thomas
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11
· 
Saint Thomas

From 849 £ per day

Hire Sailboat Dufour Yacht Dufour 430 GL Saint Thomas
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8
· 
Saint Thomas

From 714 £ per day

Hire Sailboat Jeanneau Sun Odyssey 349 Saint Thomas
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6
· 
Saint Thomas

From 462 £ per day

Hire Sailboat Dufour Yachts Dufour 460 GL Adventure with A/C Saint Thomas
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6
· 
Saint Thomas

From 712 £ per day

Hire Sailboat Bénéteau Oceanis 41.1 Saint Thomas
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6
· 
Saint Thomas

From 571 £ per day

Hire Sailboat JEANNEAU Sun Odyssey 519  with watermaker & A/C - PLUS Saint Thomas
Discount offer
11
· 
Saint Thomas

From 849 £ per day

Hire Sailboat Jeanneau Sun Odyssey 449 Saint Thomas
Discount offer
8
· 
Saint Thomas

From 679 £ per day

Hire Sailboat BENETEAU OCEANIS 430 Gran Roque
6
· 
Gran Roque

From 502 £ per day

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Where to sail in the Caribbean? 

The Caribbean offers perfect sailing conditions whether you are planning to sail the Leeward Islands like the US Virgin Islands, Guadeloupe, St. Maarten, and the British Virgin Islands, or the Windward Islands including St Lucia, Grenada, the Grenadines, and Martinique. 

No matter where you end up sailing to, we are sure you’ll fall in love with each of the island’s unique marine life, remote beaches, and waterfront towns. 

  • US Virgin Islands- From St. Thomas, St. Croix to St. John, each with its beautiful coves and inlets yet to be discovered, this is a true mecca for yachters. Enjoy the warm waters and be sure to explore the surrounding islands of Hassle Island, Water Island and Thatch Cay.
  • The Bahamas- an archipelago that connects the United States to the rest of the Caribbean. From Eleuthera, The Abacos, to The Exumas, there are countless shimmering cays and relaxing sand bars of unparalleled beauty waiting to be visited.
  • Cuba- a great sailing destination for its powdery white sands, Old Town Havana with its vintage charm and to get a feel for the Cuban way of life.
  • Guadeloupe- take the time to visit the Jacque Couseau Reserve or take a dive by Pigeon Island, this island truly is one of the world’s best kept boating secrets. 
  • Grenada- a can’t miss destination for sailing vacations. Enjoy the stunning bays of Grand Anse and the Morne Rouge Beach.
  • British Virgin Islands- with consistent trade winds and short distances between islands like Jost Van Dyke and Tortola, the BVIs are nothing less than a sailor’s delight. 
  • Saint Vincent and The Grenadines- a paradise you must see to believe! Take advantage of some of the top-rated snorkeling in the world at Tobago Cays!
  • Don’t forget to make time for some of the smaller islands. Like navigating the coasts of Martinique or dropping an anchor at South Friars Beach in St. Kitts.


What is there to see and do in the Caribbean? 

With the Caribbean’s ideal location and easy access from several international airports, it has never been so easy to visit. The region offers plenty of things to see and do during your stay, here are some of our favorites:

  • In The Bahamas, scuba dive at the ‘Dean’s Blue Hole,’ the second deepest blue hole in the world.
  • Spend some time at the Grand Cul-de-Sac Marine Natural Reserve in Guadeloupe.
  • On the British Virgin Islands, explore ‘The Baths,’ a beach with huge granite boulders.
  • Visit the US Virgin Island National Park and take a quick dip with the sea turtles in Maho Bay.
  • Grenada is home to St. George’s, a beautiful and colorful seaside town that you need to see!
  • In Martinique, spend a day basking in the sun at Saint-Anne Beach and village.
  • By boat, cruise to the stunning Salt Whistle Bay in The Grenadines.


Can I rent a sailboat in the Caribbean with a skipper? 

Yes! With Click&Boat, choose from a large selection of sailboats available for hire with skipper in the Caribbean. Forget the busy cruise ships and instead set sail at a slower pace (with a unique itinerary) on board your own private boat with crew. 

All that is left to do is sit back and relax while the skipper and crew take care of everything: navigating, docking, anchoring and even preparing meals on board. Allow your experienced skipper to show you all the greatest spots for relaxing, swimming and snorkeling. 

The request of a skipper and crew may come as an additional cost to your rental. Be sure to send a message to the boat owner to sort out details. The extra cost may be dependent on the number of crew members and the duration of the charter.


What is the best season for a sailboat charter in the Caribbean? 

The boat rental season in the Caribbean starts mid-November and usually winds down in April. It is best to avoid sailing from June to November as this is the Caribbean’s hurricane season. 

Yacht charters are always at their peak during the winter months, especially during the holidays as this is when most people tend to visit to escape the cold weather.


Hire a sailboat in the Caribbean with Click&Boat 

Whether you choose to charter with a private or professional owner, a sailboat rental in the Caribbean has never been so easy. With Click&Boat, the world’s leading boat rental service, book the boat of your dreams whether it be a bareboat charter or a crewed yacht!

Rely on the best prices, an internal messaging tool for owners and renters, as well as a knowledgeable team of advisors ready to help- because booking shouldn’t be a hassle. 

Choose to set sail with your favorite shipyard Jeanneau, Beneteau, or DuFour and discover the islands of the Caribbean, in comfort and style.

  • Sailboat
  • Motorboat
  • RIB
  • Catamaran
  • Jet ski
  • Houseboat
  • Yacht
Price
0 - 900+ £ /day
Length
0 - 60 m
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+
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+
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+
  • Super owner
Rent from well-reputed boat owners
  • Discounts
Enter your dates to display the exact discount
Engine
0 - 250 hp
Year
2001 - 2022
Radius
700 km max.
Manufacturer
Harbour
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Sailboat Charter Caribbean- An Adventure Awaits 

Enjoy the tropical bliss of the Caribbean Islands. With over 7,000 diverse and beautiful islands to discover, it’s no wonder why the Caribbean is one of the most visited holiday destinations in the world! With warm waters on average around 27°C (80°F), these pristine beaches are the perfect getaway to leave the cold behind during the winter and escape the crowds in the summer. 

With only 2% of the islands actually inhabited, book a sailing trip in the Caribbean to island hop at your own pace. Whether it be sailing the turquoise waters of the US Virgin Islands or snorkeling in the stunning archipelago of the British Virgin Islands, there’s a reason why the Caribbean is a world class sailing destination. 


How much does it cost to charter a sailboat in the Caribbean?

When it comes to sailboat charters in the Caribbean, expect the average price to vary due to a few factors. For example, the age and model of the vessel, the number of accommodated guests, the rental duration, and if the rental is during low or peak season may all affect the average costs, so be sure to take these factors into consideration when choosing your next boat rental. 

  • In the Caribbean, the cost of a sailboat rental may range from £252/day to £1,620/day (depending on the factors mentioned above). However, on average, you can expect the price to be about £1,910/week for 4 guests on board.
  • Luxury sailing yachts in the Caribbean may cost up to £13,230/day for 12 people on board.

Remember, with Click&Boat, weekly and daily sailboat rentals in the Caribbean are available.

Charter another yacht type in Caribbean

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