Yacht sailing holidays & skippered tours in Caribbean
Discover more than 18 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
18
experiences
18
experiences
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Bahamas
Starting from
€1,676
€2,095
Per person - min 2 pax
4.5
Premium
Duration:
9 days - 10 nights
Caribbean:
Grenadines & Martinique
16 travellers
Starting from
€1,629
€1,810
Per person - min 2 pax
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
2 travellers
Starting from
€1,071
€1,190
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
BVI - British Virgin Islands
8 travellers
Starting from
€1,188
€1,320
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Starting from
€1,071
€1,190
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Grenadines & Martinique
19 travellers
Starting from
€1,188
€1,320
Per person
5.0
Duration:
11 days - 11 nights
Caribbean:
Guadeloupe
2 travellers
Starting from
€1,680
Per person - min 2 pax
5.0
Duration:
7 days - 7 nights
Caribbean:
Venezuela
Starting from
€3,800
Per person
5.0
Duration:
7 days - 7 nights
Caribbean:
Venezuela
Starting from
€1,950
Per person
4.9
Duration:
9 days - 10 nights
Caribbean:
Grenadines & Martinique
5 travellers
€1,650
Per person
5.0
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
70 travellers
Starting from
€1,350
Per person - min 2 pax
4.8
Duration:
6 days - 6 nights
Caribbean:
Grenadines & Martinique
Give this experience a try!
€2,809
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
208 reviews
Discover Guadeloupe on a comfortable catamaran - All Inclusive
12/16/2024
Kamil C.
Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook
10/20/2024
Daniela H.
-
Switzerland
Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook
10/5/2024
ISabelle T.
-
Canada
EXUMA Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook
08/11/2024
Luca C.
-
Italy
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