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  1. Bali 4.6

    Bali 4.6

    Martinique

    9,7

    2023 14.28 meters

    5 Cabins 10 Berths

    Panneaux solaires, Bimini, Machine à café Nespresso

    from $5,174

    Crew
    Skipper (tip not included)

    See the boat
  2. Bali 4.6

    Bali 4.6

    Martinique

    8,3

    2024 14.28 meters

    7 Cabins 12 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $5,668

    See the boat
  3. Oceanis 35.1

    Oceanis 35.1

    Martinique

    8,1

    2019 10.45 meters

    3 Cabins 6 Berths

    Bimini, Panneaux solaires, Douche de pont

    from $2,570

    See the boat
  4. Excess 11

    Excess 11

    Guadeloupe

    8,8

    2024 11.28 meters

    6 Cabins 10 Berths

    Panneaux solaires, AIS, Eau chaude

    from $3,320

    See the boat
  5. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • 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.
  6. Lagoon 40

    Lagoon 40

    Martinique

    8,5

    2022 11.74 meters

    6 Cabins 10 Berths

    Panneaux solaires, Bimini, AIS

    from $3,696

    See the boat
  7. Nautitech Open 40

    8,3

    2018 12 meters

    6 Cabins 10 Berths

    Panneaux solaires, Douche de pont, Eau chaude

    from $1,822

    See the boat
  8. Bali Catsmart

    Bali Catsmart

    Martinique

    8,4

    2024 11.78 meters

    4 Cabins 9 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $2,545

    See the boat
  9. Excess 14

    Excess 14

    Martinique

    8,4

    2023 13.97 meters

    6 Cabins 12 Berths

    Panneaux solaires, Bimini, AIS

    from $5,321

    See the boat
  10. Oceanis 31 Q

    Oceanis 31 Q

    Martinique

    8,3

    2017 9.66 meters

    2 Cabins 6 Berths

    Bimini, Panneaux solaires, Douche de pont

    from $2,059

    See the boat
  11. Lagoon 400 S2

    Lagoon 400 S2

    Guadeloupe

    8,5

    2016 12.2 meters

    6 Cabins 10 Berths

    Bimini, Bluetooth, Barbecue

    Departures possible every day

    from $3,586

    See the boat
  12. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • 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.
  13. Lucia 40

    Lucia 40

    Guadeloupe

    8,1

    2020 11.73 meters

    4 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $1,926

    See the boat
  14. Lagoon 380

    Lagoon 380

    Martinique - Guadeloupe

    8,9

    2019 11.73 meters

    6 Cabins 10 Berths

    MP3, AIS, Douche de pont

    from $2,903

    See the boat
  15. Oceanis 43

    Oceanis 43

    Grenada

    5,0

    2009 13.3 meters

    4 Cabins 10 Berths

    Bimini, Guindeau électrique, Winch éléctrique

    from $2,463

    See the boat
  16. Lucia 40

    Lucia 40

    Guadeloupe

    8,2

    2018 11.73 meters

    4 Cabins 10 Berths

    Panneaux solaires, Bossoir d'annexe, Douche de pont

    from $2,024

    See the boat
  17. Lagoon 42

    Lagoon 42

    Martinique

    7,9

    2019 13.2 meters

    5 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $2,545

    See the boat
  18. Fountaine Pajot 44

    Fountaine Pajot 44

    Martinique - Guadeloupe

    9,5

    2025 13.26 meters

    6 Cabins 12 Berths

    Panneaux solaires, MP3, AIS

    from $6,246

    See the boat
  19. Lagoon 42

    Lagoon 42

    Guadeloupe

    8,9

    2025 13.2 meters

    6 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    Departures possible every day

    from $4,742

    See the boat
  20. First 30 Jk

    First 30 Jk

    Martinique

    7,6

    2013 9.81 meters

    2 Cabins 6 Berths

    Congélateur, Sondeur, Four

    from $1,854

    See the boat
  21. Astrea 42

    Astrea 42

    Martinique

    7,2

    2022 12.58 meters

    6 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    Departures possible every day (except Sunday)

    from $3,701

    See the boat
  22. Bali 4.2

    Bali 4.2

    Guadeloupe

    8,6

    2021 12.75 meters

    6 Cabins 10 Berths

    Panneaux solaires, Bimini, Douche de pont

    from $2,834

    See the boat
Sailboat : 1 132 boats found

Sailboat charter in the Caribbean with or without a skipper

Last updated on 3 November 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 1 389
Types of service Skipper, Hostess, Chef (meals not included), Sailor
Average price per week $14,017
Minimum weekly price $1,411
Maximum price per week $129,550

Pierre
With Pierre your cruise expert

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