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Sailing boat rentals in the Caribbean

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Sailing boat rent Beneteau First 50s in Willemstad, Curacao

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Enjoy an unforgettable holiday with this First 50s sailboat

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Sailing boat Beneteau First 50s (2017, refit 2017) 49.18 feet

Skipper included in the price

3 cabins 2 baths 10 places 6 berths Willemstad (Curacao)
from $1,350 /day
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- 10%
Sailing boat rent Beneteau First 50 in Marina Port-La-Royale, Saint Martin

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Enjoy the coast of Guadeloupe in your sailboat First 50

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Sailing boat Beneteau First 50 (2008, refit 2019) 49.21 feet

Skipper is mandatory

3 cabins 2 baths 14 places 8 berths Marina Port-La-Royale (Saint Martin)
from $1,836 $1,653 /day
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Sailing boat rent Beneteau First 50 in Marina de Bas-du-Fort, Guadeloupe

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Enjoy the coast of Saint Martin on board a Beneteau sailing boat

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Sailing boat Beneteau First 50 (2008, refit 2019) 49.21 feet

Skipper is mandatory

3 cabins 2 baths 14 places 8 berths Marina de Bas-du-Fort (Guadeloupe)
from $1,235 $1,111 /day
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Sailing boat rent Beneteau First 50 in Marina de Cohe, Martinique

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Beautiful First 50 2008 sailing boat

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Sailing boat Beneteau First 50 (2008, refit 2019) 49.21 feet

Skipper is mandatory

3 cabins 2 baths 14 places 8 berths Marina de Cohe (Martinique)
from $1,235 $1,111 /day
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- 10%
Sailing boat rent Beneteau First 50 in Nanny Cay Marina, British Virgin Islands

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A beautiful Beneteau sailboat in Guadeloupe

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Sailing boat Beneteau First 50 (2008, refit 2019) 49.21 feet

Skipper is mandatory

3 cabins 2 baths 14 places 8 berths Nanny Cay Marina (British Virgin Islands)
from $1,235 $1,111 /day
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- 20%
Sailing boat rent Beneteau Oceanis 38 in Port du Marin, Martinique

Enjoy the sea on board this Beneteau Oceanis 38 sailing boat

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Sailing boat Beneteau Oceanis 38 (2014) 36.09 feet

With or without skipper

3 cabins 1 bath 8 places 7 berths Port du Marin (Martinique)
from $344 $275 /day
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Sailing boat rent X-YATCHS X-512  in Marina Pointe à Pitre, Guadeloupe

Beautiful X-512 1991 sailing boat

Flexible cancellation or change
Sailing boat X-YATCHS X-512 (1991, refit 2014) 52.49 feet

Skipper included in the price

2 cabins 2 baths 4 places 4 berths Marina Pointe à Pitre (Guadeloupe)
from $601 /day
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Sailing boat rent Bavaria Yachtbau Bavaria 46 Cruiser in Rodney Bay Marina, Saint Lucia

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SailboatSailing holidays on a sailboat for up to 8

Flexible cancellation or change

Sailing boat Bavaria Yachtbau Bavaria 46 Cruiser (2007) 47.24 feet

With or without skipper

4 cabins 2 baths 8 places 8 berths Rodney Bay Marina (Saint Lucia)
from $617 /day
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Sailing boat rent Sun  ODYSSEY 42 I in Port du Marin, Martinique

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Rent this sailboat ODYSSEY 42 I and explore dreamy coastlines

Flexible cancellation or change
Sailing boat Sun ODYSSEY 42 I (2008) 41.31 feet

With or without skipper

3 cabins 2 baths 8 places 8 berths Port du Marin (Martinique)
from $308 /day
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Sailing boat rent Jeanneau Sun Loft 47 monocat in Anse Marcel, Saint Martin

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Enjoy the sea on board this Jeanneau Sun Loft 47 monocat sailing boat

Flexible cancellation or change
Sailing boat Jeanneau Sun Loft 47 monocat (2020) 47.31 feet

With or without skipper

7 cabins 4 baths 13 places 13 berths Anse Marcel (Saint Martin)
from $527 $475 /day
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Sailing boat rent Jeanneau Sun Loft 47 monocat in Marina de Bas-du-Fort, Guadeloupe

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Magnifique voilier Sun Loft 47 monocat 2020

Flexible cancellation or change
Sailing boat Jeanneau Sun Loft 47 monocat (2020) 47.31 feet

With or without skipper

7 cabins 4 baths 13 places 13 berths Marina de Bas-du-Fort (Guadeloupe)
from $617 $555 /day
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Sailing boat rent Dufour Yachts 460 GL Liberty in Jolly Harbour Marina, Antigua and Barbuda

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Enjoy an unforgettable holiday with this 460 GL Liberty sailboat

Flexible cancellation or change
Sailing boat Dufour Yachts 460 GL Liberty (2018) 46.42 feet

With or without skipper

4 cabins 4 baths 10 places 10 berths Jolly Harbour Marina (Antigua and Barbuda)
from $710 $639 /day
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Sailing boat rent Dufour Yacht Dufour 430 GL in Inner Harbour, British Virgin Islands

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Enjoy your trip in a 13.24 metre sailboat

Flexible cancellation or change
Sailing boat Dufour Yacht Dufour 430 GL (2020) 43.44 feet

With or without skipper

4 cabins 2 baths 10 places 10 berths Inner Harbour (British Virgin Islands)
from $445 $401 /day
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Sailing boat rent Dufour Yachts 405 L in Jolly Harbour Marina, Antigua and Barbuda

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Rent this sailing boat and get to know the beaches of Antigua and Barbuda

Flexible cancellation or change

Sailing boat Dufour Yachts 405 L (2012) 39.93 feet

With or without skipper

3 cabins 2 baths 8 places 8 berths Jolly Harbour Marina (Antigua and Barbuda)
from $302 $272 /day
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Sailing boat rent Dufour Yachts Dufour 56 with A/C in Scrub Island Resort, British Virgin Islands

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A beautiful Dufour Yachts sailboat in Scrub Island Resort

Flexible cancellation or change
Sailing boat Dufour Yachts Dufour 56 with A/C (2019) 56.27 feet

With or without skipper

4 cabins 2 baths 8 places 8 berths Scrub Island Resort (British Virgin Islands)
from $639 $575 /day
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Sailing boat rent Dufour Yachts Dufour 390 in Anse Marcel, Saint Martin

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Enjoy the coast of Saint Martin in your sailboat Dufour 390

Flexible cancellation or change

Sailing boat Dufour Yachts Dufour 390 (2019) 39.14 feet

With or without skipper

3 cabins 3 baths 8 places 8 berths Anse Marcel (Saint Martin)
from $363 $326 /day
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Sailing boat rent Bavaria Yachtbau Bavaria Cruiser 46 - 4 cab. in Nanny Cay Marina, British Virgin Islands

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Discover the coast of British Virgin Islands in this Bavaria 46 Cruiser

Flexible cancellation or change
Sailing boat Bavaria Yachtbau Bavaria Cruiser 46 - 4 cab. (2015) 46.82 feet

With or without skipper

4 cabins 3 baths 10 places 10 berths Nanny Cay Marina (British Virgin Islands)
from $461 /day
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Sailing boat rent Bavaria Yachtbau Bavaria 46 Vision in Nanny Cay Marina, British Virgin Islands

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Magnificent Bavaria 46 Vision sailboat in British Virgin Islands

Flexible cancellation or change
Sailing boat Bavaria Yachtbau Bavaria 46 Vision (2015) 45.90 feet

With or without skipper

3 cabins 2 baths 8 places 8 berths Nanny Cay Marina (British Virgin Islands)
from $543 /day
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Price depends on dates and duration of a charter Add dates for prices

All about Sailboat Rentals in the Caribbean

The Caribbean is an idyllic destination with a vibrant and authentic culture. With a warm tropical climate through winter, steady sailing winds and a range of some 7,000+ outstanding islands to hop between, you can choose everything from uninhabited and remote outcrops to bustling port town nightlife. Although there's plenty of smooth and easy sailing to be had in the Caribbean, more adventurous opportunities await in areas like St. Martin, with open-water stretches and remote anchorages. You can choose from a wide variety of rental sailing boats at good prices for your next sailing adventure.

A sailing paradise, paired with rich cultures, cuisines and traditions, the Caribbean is full of adventures and beautiful stretches of coastline where you can sail with your friends and family. Sail the British Virgin Islands and anchor in idyllic bays where you can stop for lunch or a cocktail on the beach. Snorkel with the tropical fish and turtles in the Bahamas and even encounter a swimming pig, or two! (Yes! We’re not joking!) Let yourself go as you sail with the wind in your hair and admire a constant panoramic view of breathtaking nature at its best. Rent a sailboat in the Caribbean!

How to Rent a Caribbean Sailing Boat

Renting a sailboat in the Caribbean is easy to secure and will only take a few minutes. Many visitors will choose to charter a sailboat for a week or more, either with a skipper or without, to fully explore the best of the Caribbean. As a region of colonial heritage, each island offers a unique blend of cultures. Whether that's Anglophone areas like the British Virgin Islands or Francophone Guadeloupe, it's best to choose one of the island areas to explore. You can choose to circumnavigate larger islands like Puerto Rico or stick to archipelagos and island-hopping.

Sailing areas in the Caribbean

The Caribbean is a sailors playground, with an unlimited number of routes and potential itineraries. The British Virgin Islands may offer the best flexibility, with many islands within close distance from each other, offering plenty of opportunities to sail between 25 islands and take day excursions between glorious beaches and coves to a wealth of well-maintained ports such as Nanny Cay, Inner Harbour and Joma Marina. Alternatively, Grenada, St. Vincent and the Grenadines remains another favourite destination for experienced sailors, with gentle crystalline waters, alluring cays and paradisical islands. You should also consider Antigua and Barbuda, an area famed for its open sea races with plenty of small islands to visit.

Sailing boat rentals in the Caribbean are a popular choice of boat and can be found in the following areas of the Caribbean:


  • British Virgin Islands
  • Martinique
  • Bahamas
  • Saint Martin
  • Grenada
  • Saint Vincent and the Grenadines
  • Guadeloupe
  • Antigua and Barbuda   
  • Saint Lucia 
  • Curaçao


Itinerary Ideas in the Caribbean

Lacking inspiration or need some tips? Check out our Nautal blog for sailing routes around the BVI, Martinique, Guadeloupe and much more! We calculate nautical miles in our routes and give restaurant recommendations in addition to other random facts and cool things you can do in the area.

Climate and Sailing Conditions in the Caribbean

Our favourite time of year is spring and early summer, from March to June, when the islands are in bloom and are a pleasure to sail. The trade winds are perfect at this time of year, though Christmas and Thanksgiving are also popular times of year for sailboat rentals. We do not advise sailing in August and September as this is known as hurricane season and various areas are not safe during this time of year. 

Travel Tips for the Caribbean

The best way to reach the islands is usually by plane, or alternatively you can rent a sailboat in Miami or in the near Florida and sail to Caribbean areas such as The Bahamas.  Many islands have international airports and you can fly directly or find connection flights. 
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