Where
Dates
Add your dates
Rental type
With or without a skipper
-
0 - 15+ m
0 - 400+ hp
2004 - 2024
Add dates to find your ideal boat for the best price
57 sailboats available
Charter Sailboat BENETEAU OCEANIS 48 Tortola
Tortola

Sailboat BENETEAU OCEANIS 48 14.63m 80hp (2018)

10
8
Without a skipper

Charter Sailboat BENETEAU OCEANIS 41.1 Saint Thomas
Saint Thomas

Sailboat BENETEAU OCEANIS 41.1 12.43m 45hp (2018)

8
6
With or without a skipper

Charter Sailboat Bénéteau Oceanis 41.1 Saint Thomas
Saint Thomas
New

Sailboat Bénéteau Oceanis 41.1 12.00m 45hp (2018)

8
8
With or without a skipper

From €242 per day

Charter Sailboat Moorings 46.3 Road Town
Discount offer
Road Town

Sailboat Moorings 46.3 14.60m 57hp (2019)

8
8
Super owner
Without a skipper

From €420 per day

Charter Sailboat Moorings 46.3 Road Town
Discount offer
Road Town

Sailboat Moorings 46.3 14.60m 57hp (2019)

8
8
Super owner
Without a skipper

From €480 per day

Charter Sailboat Moorings 46.3 Road Town
Discount offer
Road Town

Sailboat Moorings 46.3 14.60m 57hp (2019)

8
8
Super owner
Without a skipper

From €510 per day

Charter Sailboat Moorings 46.3 Road Town
Discount offer
Road Town

Sailboat Moorings 46.3 14.60m 57hp (2019)

8
8
Super owner
Without a skipper

From €510 per day

Charter Sailboat Sunsail 51 Road Town
Discount offer
Road Town

Sailboat Sunsail 51 15.38m 75hp (2018)

10
10
Super owner
Without a skipper

From €800 per day

Charter Sailboat Sunsail 410 Road Town
Discount offer
Road Town

Sailboat Sunsail 410 12.35m 40hp (2019)

8
8
Super owner
Without a skipper

From €300 per day

Charter Sailboat Sunsail 410 Road Town
Discount offer
Road Town

Sailboat Sunsail 410 12.35m 40hp (2019)

8
8
Super owner
Without a skipper

From €305 per day

Charter Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK British Virgin Islands
British Virgin Islands

Sailboat JEANNEAU Sun Odyssey 349 - ZAURAK 10.34m 21hp (2018)

6
6
With or without a skipper

From €583 per day

Charter Sailboat Moorings 382 Road Town
Discount offer
Road Town

Sailboat Moorings 382 11.50m 29hp (2018)

6
6
Super owner
Without a skipper

From €350 per day

Charter Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. British Virgin Islands
British Virgin Islands
New

Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. 17.12m 110hp (2024)

9
9
With or without a skipper

From €612 per day

Charter Sailboat BENETEAU FIRST 40.7 Road Town
Road Town
1.3
 (1)

Sailboat Beneteau First 40.7 12m (2008)

10
8
Without a skipper

From €333 per day

Charter Sailboat Moorings 42.1 Road Town
Discount offer
Road Town

Sailboat Moorings 42.1 12.43m 45hp (2019)

8
8
Super owner
Without a skipper

From €395 per day

Charter Sailboat  Beneteau Oceanis 48 Road Town
Road Town
New

Sailboat Beneteau Oceanis 48 14.00m 80hp (2017)

8
8
Without a skipper

From €1,036 per day

Charter Sailboat Poncin Yachts Harmony 52 Road Town
Road Town
New

Harmony 52 Sao Jorge (2007)

12
10
With a skipper

From €745 per day

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 rent 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 €280/day to €1,780/day (depending on the factors mentioned above). However, on average, you can expect the price to be about 2,120/week for 4 guests on board.
  • Luxury sailing yachts in the Caribbean may cost up to €14,670/day for 12 people on board.

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

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 rent 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 skipperto 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.


Charter 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.

Good to know

Number of sailboats:20 sailboats available
Types of sailboats:with or without a skipper
Average price: €400 per day
Minimum price: €200 per day
Maximum price: €600 per day
Manufacturers:Beneteau, Jeanneau, and more

Frequently Asked Questions about Caribbean

How much does a sailboat charter cost in Caribbean in the high season versus the low season?

The average price of chartering a sailboat in Caribbean in the high season is approximately €320 per day, while they are around €267 per day in the low season.

What is the typical daily cost of hiring a skipper in Caribbean?

The cost of hiring a skipper can differ based on the destination and the owner of the boat. In Caribbean, the typical rate of a skipper is €180 per day.

What is the typical sleeping capacity for a sailboat in Caribbean?

A sailboat in Caribbean has on average 4 berths. You can find sailboats with up to 4 berths.

What is incorporated in the price of a sailboat charter in Caribbean?

In Caribbean, the rental price for a sailboat usually includes Cockpit cushions, Coffee machine, Fishing equipment etc.

What is the number of cabins typically found on a sailboat in Caribbean?

The average number of cabins for sailboats in Caribbean is 3. For larger groups, sailboats with up to 4 cabins can also be booked.

Our client reviews
4.9 / 5
Score calculated based on 433302 reviews
See all reviews