Yacht sailing holidays & skippered tours in the Caribbean
Discover the magic of sailing holidays in the Caribbean! Get on board with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture and gastronomy.
17
experiences
4.8
Super!
Caribbean: Guadeloupe
6 days - 6 nights
One departure available
February
€730
Per person
4.8
Super!
Caribbean: Guadeloupe
7 days - 7 nights
One departure available
March
€850
Per person
4.3
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
46 departures available
February - December
Starting from
€1,250
€1,125
Per person - min 2 pax
4.9
Super!
Caribbean: Grenadines & Martinique
8 days - 9 nights
One departure available
February - March
€1,750
Per person
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
36 departures available
February - December
Starting from
€1,125
€1,013
Per person - min 2 pax
4.3
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
31 departures available
February - December
Starting from
€1,680
€1,512
Per person - min 2 pax
5.0
Caribbean: Guadeloupe
7 days - 7 nights
14 departures available
February - August
Starting from
€1,272
Per person - min 2 pax
4.3
Premium
Caribbean: Guadeloupe
6 days - 7 nights
35 departures available
February - December
Starting from
€1,125
€1,013
Per person - min 2 pax
4.3
Premium
Caribbean: Bahamas
7 days - 7 nights
31 departures available
February - December
Starting from
€1,885
€1,697
Per person - min 2 pax
4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person
Caribbean: San Blas Islands - Panama
6 days - 6 nights
12 departures available
March - October
Starting from
€1,500
€1,350
Per person
4.3
Premium
Caribbean: BVI - British Virgin Islands
6 days - 7 nights
33 departures available
February - December
Starting from
€1,250
€1,125
Per person - min 2 pax
Why book a holiday with Sailsquare?
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
Get onboard solo, with your family or your friends
Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
Find out before you book who's waiting for you on board
Find out more about the skipper and travellers who have already booked the holiday, to find out more about the
Sailing holidays that suit all budgets
On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.
Reviews - Yacht sailing holidays & skippered tours in the Caribbean
231 reviews
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
01/26/2026
Sabrina B.
-
Italy
Unforgettable Mini Flotilla in the Caribbean - Dominica and Guadeloupe
01/26/2026
Giulia V.
-
Italy
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
01/19/2026
Elena B.
-
Italy
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
01/17/2026
Paola C.
-
Italy
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From Cuba to the Grenadines, via the fascinating Bahamas and the green Antilles: Martinique, Dominica and Guadeloupe. Either way, a dream trip to tropical islands.
Guide to the Caribbean by catamaran
What are the best times to go to the Caribbean? What climate will I find?
Caribbean weather and climate guide
Crystal-clear waters, rich seabed, lush vegetation and expanses of white sand are the main features of this paradise, which is a must-visit aboard a sailboat!
Guide to the BVI's by catamaran
Une constellation d'îles immergées dans une mer cristalline allant du vert au bleu profond : les fonds marins limpides cachent un trésor qui n'est pas seulement celui des pirates..
Guide to the Grenadines by catamaran
Un voyage en catamaran aux Bahamas est une expérience extraordinaire qui mêle aventure et détente au sein d'un incroyable patrimoine naturel.
Guide to the Bahamas by catamaran
Caribbean: the most beautiful places to sail
Caribbean: departures by month
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