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  1. Bali Catsmart

    Bali Catsmart

    Saint Martin - French side

    8,1

    2024 11.78 meters

    6 Cabins 10 Berths

    Panneaux solaires, Barbecue, Bossoir d'annexe

    from $2,962

    See the boat
  2. Lagoon 450 F

    Lagoon 450 F

    Guadeloupe - Martinique

    8,9

    2019 14.52 meters

    6 Cabins 12 Berths

    Panneaux solaires, Bimini, AIS

    from $5,385

    See the boat
  3. Lagoon 380

    Lagoon 380

    Martinique

    7,8

    2020 11.73 meters

    4 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    Departures possible every day (except Sunday)

    from $2,575

    See the boat
  4. Bali Catsmart

    Bali Catsmart

    Martinique

    9,2

    2023 11.78 meters

    6 Cabins 10 Berths

    Panneaux solaires, Palmes-masques-tubas, Stabilité

    from $3,219

    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. Bali Catspace

    Bali Catspace

    Martinique

    8,9

    2024 12.33 meters

    4 Cabins 10 Berths

    Panneaux solaires, Stabilité, Espace

    from $3,629

    See the boat
  7. Excess 12

    Excess 12

    Martinique

    8,5

    2020 11.73 meters

    3 Cabins 8 Berths

    Panneaux solaires, Grand voile lattée, Guindeau électrique

    from $2,458

    See the boat
  8. Astrea 42

    Astrea 42

    Martinique

    8,5

    2024 12.58 meters

    3 Cabins 6 Berths

    Panneaux solaires, AIS, Winch éléctrique

    from $3,073

    See the boat
  9. Bali 4.6

    Bali 4.6

    Martinique

    6,4

    2022 14.28 meters

    6 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $3,863

    See the boat
  10. Lucia 40

    Lucia 40

    British Virgin Islands - BVI

    9,4

    2020 11.73 meters

    3 Cabins 8 Berths

    Bain de soleil, Barbecue, Douche de pont

    from $3,518

    See the boat
  11. Elba 45

    Elba 45

    Martinique

    9,3

    2025 13.45 meters

    4 Cabins 9 Berths

    Panneaux solaires, MP3, AIS

    from $6,005

    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. Lagoon 46

    Lagoon 46

    Guadeloupe

    8,5

    2023 13.99 meters

    6 Cabins 12 Berths

    Panneaux solaires, Bluetooth, Barbecue

    Departures possible every day

    from $5,853

    See the boat
  14. Bali Catspace

    Bali Catspace

    Martinique

    8,4

    2024 12.33 meters

    4 Cabins 10 Berths

    Panneaux solaires, Bimini, Bluetooth

    from $2,927

    See the boat
  15. Elba 45

    Elba 45

    Martinique - Guadeloupe

    9,3

    2021 13.45 meters

    6 Cabins 12 Berths

    Panneaux solaires, MP3, AIS

    from $6,005

    See the boat
  16. Bali 4.3

    Bali 4.3

    Guadeloupe

    8,4

    2020 13.1 meters

    6 Cabins 12 Berths

    Flybridge, Panneaux solaires, Bossoir d'annexe

    from $2,698

    See the boat
  17. Lagoon 450 F

    Lagoon 450 F

    Saint Vincent - Martinique

    7,5

    2017 14.52 meters

    6 Cabins 12 Berths

    Flybridge, Bimini, Barbecue

    Departures possible every day

    from $7,843

    See the boat
  18. Lagoon 380

    Lagoon 380

    Guadeloupe

    9,5

    2016 11.73 meters

    6 Cabins 10 Berths

    Bain de soleil, Panneaux solaires, Bimini

    Departures possible every day

    from $3,512

    See the boat
  19. Sun Odyssey 42i

    9,2

    2008 13.19 meters

    3 Cabins 6 Berths

    Bimini, Guindeau électrique, Panneaux solaires

    Departures possible every day

    from $2,458

    See the boat
  20. Bali Catsmart

    Bali Catsmart

    Saint Martin - French side

    7,1

    2024 11.78 meters

    6 Cabins 10 Berths

    Panneaux solaires, Barbecue, Bossoir d'annexe

    from $6,023

    See the boat
  21. Isla 40

    Isla 40

    Guadeloupe - Martinique

    9,0

    2021 11.93 meters

    5 Cabins 11 Berths

    MP3, AIS, Douche de pont

    from $3,734

    See the boat
  22. Oceanis 43

    Oceanis 43

    Grenada

    5,0

    2009 13.3 meters

    4 Cabins 10 Berths

    Bimini, Guindeau électrique, Winch éléctrique

    from $2,492

    See the boat
Sailboat : 1 096 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 1 362
Types of service Skipper, Hostess, Chef (meals not included), Sailor
Average price per week $14,019
Minimum weekly price $1,428
Maximum price per week $131,107

Pierre
With Pierre your cruise expert

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