Yacht sailing holidays & skippered tours in Caribbean
Discover more than 5 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
5
experiences
5
experiences
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Bahamas
+16 travellers
have booked
Starting from
€1,430
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
+2 travellers
have booked
Starting from
€1,150
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
+4 travellers
have booked
Starting from
€1,420
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+4 travellers
have booked
Starting from
€1,280
Per person
4.6
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
has booked
Starting from
€1,150
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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 Caribbean
203 reviews
Guadeloupe and its islands in ten days
02/10/2024
Caterina P.
-
Italy
Guadeloupe and its islands in ten days
02/9/2024
Franck P.
-
France
Guadeloupe and its islands in ten days
02/8/2024
Lucie C.
-
France
Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook
02/5/2024
MARIO I.
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