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All inclusive yacht sailing holidays & tours in Caribbean

Discover more than 16 opportunities to get on board a All inclusive adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

06/30/2025

Beatrice S.

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Spain

You couldn't expect more than one trip. The big new catamaran. A/C whenever needed and plenty of water. Captain Lutius could not be more professional and friendly. He made us all feel comfortable and always proposing to do different activities in a fun and casual atmosphere. Karin, the chef equally nice and funny. Very professional and attentive to our needs. The places we visited in a dream and despite some rains in general have been worth sailing out of season as we are practically alone in the most amazing places. We have always been lucky with the rest of the clients and in this case it has not been different and despite being mostly French-speaking we have communicated very well in English.
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BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

04/12/2025

Carla P.

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Italy

Great skipper and great service on board with excellent food
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BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

03/18/2025

Patricia A. Mcmahon s.

Wonderful trip. I just wish we saw more of the islands we snorkel by.
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BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

02/24/2025

Stefania T.

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Italy

Other experiences with you have been made with newer and more comfortable boats. I suggest adapting all the boats so as to justify the fairly high cost of the cruise.

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