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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 12 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

February

€730

Per person

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4.9

Super!

Under the Caribbean sun on a catamaran

Caribbean: Grenadines & Martinique

8 days - 9 nights

One departure available

February - March

€1,750

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

January - March

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

February - March

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

January - March

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

2 departures available

February

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

4 departures available

January - March

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

January - March

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

One departure available

February

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

January - March

Starting from

€1,250

€1,125

Per person - min 2 pax

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5.0

San Blas Paradise Crociera All Inclusive

Caribbean: San Blas Islands - Panama

4 days - 4 nights

One departure available

February

€700

Per person

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

One departure available

February - March

Starting from

€3,000

€2,100

Per person

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

229 reviews

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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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New Year's Eve 2026 discovering the Lesser Antilles by catamaran

01/15/2026

Deborah C.

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Italy

Super-comfortable catamaran Itinerary definitely improvable Good organization Good skipper
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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

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