All inclusive yacht sailing holidays & tours in Caribbean
Discover more than 15 opportunities to get on board a All inclusive adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.
15
experiences
15
experiences
4.3
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
53 departures available
January - December
Starting from
€1,680
€1,512
Per person - min 2 pax
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
59 departures available
January - December
Starting from
€1,125
€1,013
Per person
4.3
Premium
Caribbean: BVI - British Virgin Islands
6 days - 7 nights
55 departures available
January - December
Starting from
€1,250
€1,125
Per person
4.3
Premium
Caribbean: Guadeloupe
6 days - 7 nights
57 departures available
January - December
Starting from
€1,125
€1,013
Per person
4.3
Premium
Caribbean: Bahamas
6 days - 7 nights
10 departures available
July - December
Starting from
€1,865
Per person
5.0
Caribbean: Guadeloupe
7 days - 7 nights
21 departures available
January - December
Starting from
€1,272
Per person - min 2 pax
Caribbean: Trinidad and Tobago
14 days - 14 nights
One departure available
October
€2,300
Per person
4.3
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
76 departures available
January - December
Starting from
€1,250
€1,125
Per person
5.0
Caribbean: San Blas Islands - Panama
7 days - 7 nights
One departure available
July
€1,750
Per person
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
2 departures available
January
Starting from
€2,490
Per person - min 2 pax
4.3
Premium
Caribbean: Bahamas
7 days - 7 nights
37 departures available
January - December
Starting from
€1,885
€1,697
Per person - min 2 pax
5.0
Caribbean: San Blas Islands - Panama
7 days - 7 nights
3 departures available
July - August
€1,167
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 - All inclusive yacht sailing holidays & tours in Caribbean
34 reviews
Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook
06/30/2025
Beatrice S.
-
Spain
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 & SupportCaribbean: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964