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.
24
experiences
24
experiences
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
Starting from
€1,760
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Saint Martin
+2 travellers
Have booked
Starting from
€1,630
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Bahamas
+16 travellers
Have booked
Starting from
€1,795
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+2 travellers
Have booked
Starting from
€1,560
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Has booked
Starting from
€1,320
Per person
5.0
Duration:
7 days - 7 nights
Caribbean:
San Blas Islands - Panama
Liane F.
Has booked
€1,560
Per person
4.2
Premium
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
+14 travellers
Have booked
Starting from
€2,055
Per person
4.8
Duration:
10 days - 10 nights
Caribbean:
Antigua and Barbuda
+6 travellers
Have booked
€1,790
Per person
4.0
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
+7 travellers
Have booked
Starting from
€1,750
Per person
4.8
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
+11 travellers
Have booked
€1,664
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
+6 travellers
Have booked
Starting from
€1,525
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+2 travellers
Have booked
Starting from
€1,465
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
172 reviews
Paradise on a sailing boat with All Inclusive
07/19/2023
Liane F.
-
Brazil
Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook
05/7/2023
Rob H.
EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook
03/30/2023
Gianluca C.
7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board
03/28/2023
Thomas T.
-
Austria
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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
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