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.
17
experiences
17
experiences
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
6 travellers
Starting from
€1,071
€1,190
Per person
4.4
Premium
Duration:
9 days - 10 nights
Caribbean:
Grenadines & Martinique
22 travellers
Starting from
€1,629
€1,810
Per person - min 2 pax
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Starting from
€1,071
€1,190
Per person
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Grenadines & Martinique
26 travellers
Starting from
€1,188
€1,320
Per person
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
BVI - British Virgin Islands
22 travellers
Starting from
€1,188
€1,320
Per person
4.9
Duration:
7 days - 7 nights
Caribbean:
ABC Islands: Aruba, Bonnaire, Curaçao
Give this experience a try!
€450
Per person
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Bahamas
30 travellers
Starting from
€1,865
Per person
5.0
Duration:
11 days - 11 nights
Caribbean:
Guadeloupe
2 travellers
Starting from
€1,795
Per person - min 2 pax
4.9
Duration:
8 days - 9 nights
Caribbean:
Grenadines & Martinique
Give this experience a try!
€1,750
Per person
5.0
Duration:
7 days - 7 nights
Caribbean:
San Blas Islands - Panama
Give this experience a try!
€1,750
Per person
4.4
Premium
Duration:
6 days - 7 nights
Caribbean:
Saint Martin
Starting from
€2,490
Per person - min 2 pax
5.0
Duration:
11 days - 11 nights
Caribbean:
Grenada
Give this experience a try!
€1,795
Per person - min 2 pax
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 the Caribbean
218 reviews
12 day Cruising/Sailing Experience around St. Martin and St. Barth's
04/17/2025
Basiel B.
-
United States
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
04/12/2025
Carla P.
-
Italy
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
03/18/2025
Patricia A. Mcmahon s.
BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook
02/24/2025
Stefania T.
-
Italy
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & Support
Can't find the perfect holiday for you?
Tell us what you are looking for and let our team find the right solution for you!
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
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
