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OUR COMMITMENTS
Jakob
Jakob
Your dedicated advisor
  • 30 years of experience
    • An expert dedicated to your cruise project
    • This longevity is a guarantee of quality and reliability.
  • Total transparency
    • A comprehensive overview of the boats of all the yacht charter companies present at each destination
    • Our goal is to tell our customers EVERYTHING about the quality of the boats, the partners and the risks associated with the cruise.
  • A single concierge service
    • A friendly and responsive service by phone or email until you return from your cruise
    • Everything is done to ensure that the preparation of your cruise runs smoothly. A team of 6 people is dedicated to the Experience: Support, Contract Modifications, Advice, After-Sales Service.
  • Strong commitments
    • Values that are close to our hearts
    • Filovent defends and promotes freedom and respect for all and for the customer, diversity, the environment, laws and rules.
Excellent
152 opinion on
Yacht charter Sailboat Sailboat charter The Caribbean

1 070 boats

Sun Loft 47

Guadeloupe

9,7

2020 14 meters

7 Cabs 12 Berths

Electric windlass, Cockpit cushions, Mainsail on furler

from $1,435

See the boat

Dufour 390 GL

Guadeloupe

8,3

2019 11.93 meters

3 Cabs 8 Berths

Fully battened mainsail, Fan, Deck shower

from $1,506

See the boat

Dufour 412 GL

Guadeloupe

8,3

2018 13 meters

3 Cabs 8 Berths

Fully battened mainsail, Electric windlass, Electric converter

from $1,535

See the boat

8,8

2018 12 meters

6 Cabs 10 Berths

Solar panels, Deck shower, Hot water

from $1,558

See the boat
Need advice?
Jakob
Jakob your cruise expert
Jakob will help you find the cruise that suits your needs
  • Let's find the best cruise together thanks to our 30 years of experience
  • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.

Lucia 40

Guadeloupe

7,3

2018 11.73 meters

4 Cabs 10 Berths

Solar panels, Dinghy davit, Deck shower

from $1,641

See the boat

Dufour 460 GL

Guadeloupe

8,7

2018 14.15 meters

4 Cabs 10 Berths

Fully battened mainsail, Electric windlass, Cockpit cushions

from $1,658

See the boat

Bali 4.1

Saint Martin - French side

8,3

2019 12.37 meters

6 Cabs 12 Berths

Solar panels, Dinghy davit, Deck shower

from $1,693

See the boat

Lagoon 40

Tortola

7,0

2019 11.74 meters

6 Cabs 12 Berths

Solar panels, Deck shower, Electric winch

from $1,793

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Excess 11

Saint Martin - French side

9,7

2023 11.28 meters

6 Cabs 12 Berths

Solar panels, AIS (Automatic Identification System), Dinghy davit

from $1,810

See the boat

Lucia 40

Guadeloupe

7,7

2020 11.73 meters

4 Cabs 10 Berths

Solar panels, Bluetooth, Dinghy davit

from $1,851

See the boat
Need advice?
Jakob
Jakob your cruise expert
Jakob will help you find the cruise that suits your needs
  • Let's find the best cruise together thanks to our 30 years of experience
  • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.

First 30 Jk

Martinique

7,3

2013 9.81 meters

2 Cabs 6 Berths

Freezer, Depth sounder, Oven

from $1,878

See the boat

Dufour 390 GL

Martinique

6,8

2019 11.93 meters

3 Cabs 8 Berths

Fully battened mainsail, Fan, Deck shower

from $1,898

See the boat

Lagoon 40

Saint Martin - French side

8,3

2022 11.74 meters

6 Cabs 12 Berths

Solar panels, Dinghy davit, Deck shower

from $1,904

See the boat

Dufour 412 GL

Martinique

7,1

2018 13 meters

3 Cabs 8 Berths

Fully battened mainsail, Electric windlass, Electric converter

from $1,904

See the boat

Dufour 412 GL

Martinique

6,7

2018 13 meters

3 Cabs 8 Berths

Fully battened mainsail, Electric windlass, Electric converter

from $1,910

See the boat

7,7

2018 10.28 meters

2 Cabs 5 Berths

Teak cockpit, Fully battened mainsail, Deck shower

from $1,916

See the boat

Lucia 40

Guadeloupe

6,7

2020 11.73 meters

4 Cabs 10 Berths

Solar panels, Dinghy davit, Deck shower

from $1,933

See the boat

Lagoon 380

Martinique

9,8

2019 11.5 meters

4 Cabs 10 Berths

Solar panels, Dinghy davit, Deck shower

from $1,957

See the boat

Bali 4.0

Guadeloupe

8,3

2018 12.2 meters

6 Cabs 10 Berths

Solar panels, Dinghy davit, Deck shower

from $1,969

See the boat

Mahe 36

Martinique

9,1

2015 11 meters

3 Cabs 6 Berths

Solar panels, Bimini, Barbecue

from $1,992

See the boat
Sailboat : 1 070 boats found

Sailboat charter in the Caribbean with or without a skipper

Last updated on 30 July 2025

 

With family or friends, a sailboat charter in The Caribbean will offer you an unforgettable experience. As well as enjoying the winter sun, you will be delighted to contemplate the breathtaking landscapes throughout the journey that will take you to exceptional places such as the Virgin Islands, Guadeloupe, Martinique and the Grenadines.

Why go on a sailing trip to the Caribbean?

Cradled by the Caribbean Sea, the Caribbean is a paradise that you will love to discover. In addition to an exceptionally mild climate, this charming archipelago will charm you with the immensity and richness of its heritage inherited from colonization. From the splendid beaches of Aruba to the hiking trails of Guadeloupe, via the magnificent and isolated beaches of Martinique, there is a variety of activities to which you can veer while visiting its main islands.

The best places to sail in The Caribbean

Aboard a sailboat charter with a skipper who knows the region very well, you will have the privilege of discovering superb anchorages. Apart from the Virgin Islands and the Grenadines, San Salvador is one of the tourist spots not to be missed. This destination has beautiful sandy beaches that will be appreciated by those who like to relax, who can swim while enjoying the winter sun.

Practical information on sailing in the area

Overall, the various islands that make up The Caribbean offer excellent conditions for sailing. This is particularly the case of Martinique, with temperatures of between 25 and 30°C, and the particular feature that they do not vary much throughout the year. In this area, there are also numerous anchorages with or without mooring posts, some of which are subject to a charge. Although it is pleasant to sail all year round in this corner of paradise, the period from December to April is the most favorable for organizing a sailing cruise with or without a skipper in The Caribbean.

Good to know

Number of boats available 1 326
Types of service Skipper, Hostess, Chef (meals not included), Sailor
Average price per week $96,969
Minimum weekly price $1,435
Maximum price per week $87,893,793

Jakob
Jakob your cruise expert
Contact our advisors to find your future cruise
  • Let's find the best cruise together thanks to our 30 years of experience
  • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.

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