Boat rental > Sailing boats > Caribbean

Sailing boat rentals in the Caribbean

42710 reviews

- 15%
Sailing boat rent Beneteau Oceanis 38 in Port du Marin, Martinique

Sailing boat rent Beneteau Oceanis 38 in Port du Marin, Martinique (2014)

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 $453 $385 /day
View boat
- 10%
Sailing boat rent Beneteau First 50 in Marina Port-La-Royale, Saint Martin

Sailing boat rent Beneteau First 50 in Marina Port-La-Royale, Saint Martin (2008 refit 2019)

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 $1,767 $1,590 /day
View boat
- 10%
Sailing boat rent Beneteau First 50 in Marina de Bas-du-Fort, Guadeloupe

Sailing boat rent Beneteau First 50 in Marina de Bas-du-Fort, Guadeloupe (2008 refit 2019)

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 $1,188 $1,069 /day
View boat
Price depends on dates and duration of a charter Add dates for prices
- 10%
Sailing boat rent Beneteau First 50 in Marina de Cohe, Martinique

Sailing boat rent Beneteau First 50 in Marina de Cohe, Martinique (2008 refit 2019)

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 $1,188 $1,069 /day
View boat
- 10%
Sailing boat rent Beneteau First 50 in Nanny Cay Marina, British Virgin Islands

Sailing boat rent Beneteau First 50 in Nanny Cay Marina, British Virgin Islands (2008 refit 2019)

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 $1,188 $1,069 /day
View boat
Sailing boat rent X-YATCHS X-512  in Marina Pointe à Pitre, Guadeloupe

Sailing boat rent X-YATCHS X-512 in Marina Pointe à Pitre, Guadeloupe (1991 refit 2014)

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 $658 /day
View boat
Sailing boat rent Sun  ODYSSEY 42 I in Port du Marin, Martinique

Instant book

Sailing boat rent Sun ODYSSEY 42 I in Port du Marin, Martinique (2008)

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 $311 /day
View boat
Sailing boat rent Sun Sun Odyssey 36i in Port du Marin, Martinique

Instant book

Sailing boat rent Sun Sun Odyssey 36i in Port du Marin, Martinique (2008)

Sailing boat Sun Sun Odyssey 36i (2008) 35.07 feet

With or without skipper

3 cabins 1 bath 8 places 8 berths Port du Marin (Martinique)
from $280 /day
View boat
Price depends on dates and duration of a charter Add dates for prices
Sailing boat rent Bavaria Yachtbau Bavaria 46 Cruiser in Rodney Bay Marina, Saint Lucia

Instant book

Sailing boat rent Bavaria Yachtbau Bavaria 46 Cruiser in Rodney Bay Marina, Saint Lucia (2007)


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 $624 /day
View boat
- 10%
Sailing boat rent Jeanneau Sun Loft 47 - 6 + 1 cab. in Marina de Bas-du-Fort, Guadeloupe

Instant book

Sailing boat rent Jeanneau Sun Loft 47 - 6 + 1 cab. in Marina de Bas-du-Fort, Guadeloupe (2020)

Sailing boat Jeanneau Sun Loft 47 - 6 + 1 cab. (2020) 47.31 feet

With or without skipper

6 cabins 4 baths 13 places 13 berths Marina de Bas-du-Fort (Guadeloupe)
from $608 $547 /day
View boat
Sailing boat rent Bavaria Yachtbau Bavaria Cruiser 46 - 4 cab. in Rodney Bay Marina, Saint Lucia

Instant book

Sailing boat rent Bavaria Yachtbau Bavaria Cruiser 46 - 4 cab. in Rodney Bay Marina, Saint Lucia (2017)

Sailing boat Bavaria Yachtbau Bavaria Cruiser 46 - 4 cab. (2017) 46.82 feet

With or without skipper

4 cabins 2 baths 8 places 8 berths Rodney Bay Marina (Saint Lucia)
from $717 /day
View boat
Sailing boat rent Beneteau Oceanis 413 in Rodney Bay Marina, Saint Lucia

Instant book

Sailing boat rent Beneteau Oceanis 413 in Rodney Bay Marina, Saint Lucia (2009)

Sailing boat Beneteau Oceanis 413 (2009) 39.99 feet

With or without skipper

3 cabins 2 baths 6 places 6 berths Rodney Bay Marina (Saint Lucia)
from $468 /day
View boat
Sailing boat rent Jeanneau Sun Odyssey 32i in Rodney Bay Marina, Saint Lucia

Instant book

Sailing boat rent Jeanneau Sun Odyssey 32i in Rodney Bay Marina, Saint Lucia (2007)

Sailing boat Jeanneau Sun Odyssey 32i (2007) 31.50 feet

With or without skipper

2 cabins 1 bath 4 places 4 berths Rodney Bay Marina (Saint Lucia)
from $296 /day
View boat
Price depends on dates and duration of a charter Add dates for prices
Sailing boat rent Bavaria Yachtbau Bavaria Cruiser 50 - 4 cab. in Rodney Bay Marina, Saint Lucia

Instant book

Sailing boat rent Bavaria Yachtbau Bavaria Cruiser 50 - 4 cab. in Rodney Bay Marina, Saint Lucia (2013)

Sailing boat Bavaria Yachtbau Bavaria Cruiser 50 - 4 cab. (2013) 51.08 feet

With or without skipper

4 cabins 3 baths 8 places 8 berths Rodney Bay Marina (Saint Lucia)
from $764 /day
View boat
Sailing boat rent Bavaria Yachtbau Bavaria 46 Vision in Nanny Cay Marina, British Virgin Islands

Instant book

Sailing boat rent Bavaria Yachtbau Bavaria 46 Vision in Nanny Cay Marina, British Virgin Islands (2015)

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 $522 /day
View boat
Sailing boat rent Jeanneau Sun Odyssey 509 - 3 cab. in Nanny Cay Marina, British Virgin Islands

Instant book

Sailing boat rent Jeanneau Sun Odyssey 509 - 3 cab. in Nanny Cay Marina, British Virgin Islands (2014)

Sailing boat Jeanneau Sun Odyssey 509 - 3 cab. (2014) 50.46 feet

With or without skipper

3 cabins 2 baths 6 places 6 berths Nanny Cay Marina (British Virgin Islands)
from $505 /day
View boat
Sailing boat rent Jeanneau Sun Loft 47 - 6 + 1 cab. in Nanny Cay Marina, British Virgin Islands

Instant book

Sailing boat rent Jeanneau Sun Loft 47 - 6 + 1 cab. in Nanny Cay Marina, British Virgin Islands (2020)

Sailing boat Jeanneau Sun Loft 47 - 6 + 1 cab. (2020) 47.31 feet

With or without skipper

6 cabins 4 baths 12 places 13 berths Nanny Cay Marina (British Virgin Islands)
from $505 /day
View boat
Sailing boat rent Jeanneau Sun Odyssey 469  in Nanny Cay Marina, British Virgin Islands

Instant book

Sailing boat rent Jeanneau Sun Odyssey 469 in Nanny Cay Marina, British Virgin Islands (2013)

Sailing boat Jeanneau Sun Odyssey 469 (2013) 46.10 feet

With or without skipper

4 cabins 4 baths 10 places 10 berths Nanny Cay Marina (British Virgin Islands)
from $513 /day
View boat
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. 
This website uses cookies, by staying here you agree to our use of them. You can read more about their use in our privacy policy. More information.