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.
18
experiences
18
experiences
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
has left
Starting from
€1,047
€1,610
Per person
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
have left
Starting from
€1,629
€1,810
Per person - min 2 pax
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Grenadines & Martinique
9 travellers
have left
Starting from
€1,188
€1,320
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
2 travellers
have left
Starting from
€1,071
€1,190
Per person
4.5
Premium
Duration:
6 days - 7 nights
Caribbean:
BVI - British Virgin Islands
6 travellers
have left
Starting from
€1,188
€1,320
Per person
4.8
Super!
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
16 travellers
have left
Starting from
€1,330
€1,400
Per person
5.0
Duration:
11 days - 11 nights
Caribbean:
Guadeloupe
2 travellers
have left
Starting from
€1,680
Per person - min 2 pax
4.2
Duration:
10 days - 11 nights
Caribbean:
Grenadines & Martinique
4 travellers
have left
€1,590
Per person
4.6
Duration:
7 days - 7 nights
Caribbean:
Bahamas
8 travellers
have left
€1,690
Per person
4.9
Duration:
9 days - 10 nights
Caribbean:
Grenadines & Martinique
5 travellers
have left
€1,650
Per person
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
8 travellers
have left
Starting from
€999
Per person
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
207 reviews
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
Sail with us in the heart of the Paradise called the Grenadines
04/30/2024
Paolo G.
-
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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