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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 10 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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4.3

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

5 departures available

May - June

Starting from

€1,250

€1,125

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

May - June

Starting from

€1,205

€1,085

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

May - June

Starting from

€1,680

€1,512

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

May - June

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

3 departures available

May

Starting from

€1,272

Per person - min 2 pax

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4.3

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ABACO Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

4 departures available

May

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

4 departures available

May

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

5 departures available

May - June

Starting from

€1,250

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

May - June

Starting from

€2,544

Per person - min 2 pax

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

2 departures available

May - June

€3,000

Per person

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 - Yacht sailing holidays & skippered tours in Caribbean

232 reviews

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Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

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United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!
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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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