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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 14 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

One departure available

March

€730

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

One departure available

March

€850

Per person

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4.3

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

5 departures available

February - April

Starting from

€1,250

€1,125

Per person - min 2 pax

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4.3

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

3 departures available

March - April

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

5 departures available

February - April

Starting from

€1,125

€1,013

Per person - min 2 pax

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

One departure available

March

Starting from

€1,272

Per person - min 2 pax

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4.3

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

5 departures available

February - April

Starting from

€1,125

€1,013

Per person - min 2 pax

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4.3

Premium

ABACO Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

5 departures available

February - April

Starting from

€1,885

€1,697

Per person - min 2 pax

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A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

3 departures available

March

Starting from

€1,500

€1,350

Per person

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4.3

Premium

BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

3 departures available

February - April

Starting from

€1,250

€1,125

Per person - min 2 pax

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5.0

Grenadines Odyssey: Grenadines Islands Catamaran Cruise

Caribbean: Grenadines & Martinique

10 days - 11 nights

One departure available

March

Starting from

€2,544

Per person - min 2 pax

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5.0

12 day Cruising/Sailing Experience around St. Martin and St. Barth's

Caribbean: Saint Martin

11 days - 11 nights

One departure available

March

€1,795

Per person - min 2 pax

Why book a holiday with Sailsquare?

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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 - Yacht sailing holidays & skippered tours in Caribbean

231 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/26/2026

Sabrina B.

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Italy

Fantastic experience and very qualified staff. Maybe I thought I would see more beaches but in general I was very satisfied.
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Unforgettable Mini Flotilla in the Caribbean - Dominica and Guadeloupe

01/26/2026

Giulia V.

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Italy

Andrea and Federico are true professionals and always kind and very nice, capable and cheerful sailors, nautical experts and entertainers. Beautiful holiday, fun and in complete safety!
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/19/2026

Elena B.

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Italy

Amazing experience! Skipper (Medhi) and Cook (Kris) super capable smart and funny ♥️
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/17/2026

Paola C.

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Italy

Very nice experience overall the only thing for the destination maybe it is better to do more days as the last three days we did too much sailing in the afternoon, it would have been better to travel at night / early morning or possibly do more days in the Tobago cas area, Skipper very nice and quiet, the steward perhaps a little too young did not have a great desire to clean and lacked the eye of a person with more experience. Overall I would do it again

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