
Catamaran yacht sailing holidays & tours in the Caribbean
Get on board on your dream catamaran cruise in the Caribbean! Travel in comfort with your partner, friends or family to discover Cuba, the Bahamas, the Grenadines, Guadeloupe and the Virgin Islands.
14
experiences

4.3
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
53 departures available
January - December
Starting from
€1,250
€1,125
Per person

4.3
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
36 departures available
January - December
Starting from
€1,680
€1,512
Per person - min 2 pax

4.5
Caribbean: Guadeloupe
12 days - 12 nights
One departure available
December - January
€2,150
Per person

5.0
Caribbean: Grenadines & Martinique
11 days - 11 nights
One departure available
December
€1,559
Per person

4.9
Caribbean: Grenadines & Martinique
8 days - 9 nights
2 departures available
February - March
€1,750
Per person

4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
44 departures available
January - December
Starting from
€1,125
€1,013
Per person

4.3
Premium
Caribbean: Guadeloupe
6 days - 7 nights
43 departures available
January - December
Starting from
€1,125
€1,013
Per person

4.3
Premium
Caribbean: Bahamas
6 days - 7 nights
2 departures available
November - December
Starting from
€1,985
Per person

5.0
Caribbean: Guadeloupe
7 days - 7 nights
18 departures available
January - December
Starting from
€1,272
Per person - min 2 pax

4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
One departure available
January
Starting from
€2,690
Per person - min 2 pax

4.3
Premium
Caribbean: Bahamas
7 days - 7 nights
36 departures available
January - December
Starting from
€1,885
€1,697
Per person - min 2 pax

4.3
Premium
Caribbean: BVI - British Virgin Islands
6 days - 7 nights
43 departures available
January - December
Starting from
€1,250
€1,125
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 - Catamaran yacht sailing holidays & tours in the Caribbean
112 reviews
GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD
10/28/2025
Anne-Marie G.
-
Curaçao
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
06/30/2025
Beatrice S.
-
Spain
BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD
04/12/2025
Carla P.
-
Italy
BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD
03/18/2025
Patricia A. Mcmahon s.
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