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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 17 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

17

experiences

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4.4

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

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4 travellers

Starting from

€1,071

€1,190

Per person

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4.4

Premium

GRENADINES 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

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22 travellers

Starting from

€1,629

€1,810

Per person - min 2 pax

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4.4

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Starting from

€1,071

€1,190

Per person

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4.4

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Grenadines & Martinique

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26 travellers

Starting from

€1,188

€1,320

Per person

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4.4

Premium

BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Duration:

6 days - 7 nights

Caribbean:

BVI - British Virgin Islands

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22 travellers

Starting from

€1,188

€1,320

Per person

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4.9

Beaches and entertainment: sailing between Curaçao and Bonaire

Duration:

7 days - 7 nights

Caribbean:

ABC Islands: Aruba, Bonnaire, Curaçao

Give this experience a try!

€450

Per person

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4.4

Premium

EXUMA Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Bahamas

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30 travellers

Starting from

€1,865

Per person

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5.0

12 days of sailing from Martinique to Guadeloupe

Duration:

11 days - 11 nights

Caribbean:

Guadeloupe

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2 travellers

Starting from

€1,795

Per person - min 2 pax

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4.9

Under the Caribbean sun on a catamaran

Duration:

8 days - 9 nights

Caribbean:

Grenadines & Martinique

Give this experience a try!

€1,750

Per person

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5.0

Paradise on a sailing boat with All Inclusive

Duration:

7 days - 7 nights

Caribbean:

San Blas Islands - Panama

Give this experience a try!

€1,750

Per person

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4.4

Premium

New Year's Eve catamaran in the golden triangle of the Caribbean - Full board with hostess

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

Starting from

€2,490

Per person - min 2 pax

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5.0

12 days/11 nights around Grenada and the Grenadines

Duration:

11 days - 11 nights

Caribbean:

Grenada

Give this experience a try!

€1,795

Per person - min 2 pax

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

218 reviews

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

04/17/2025

Basiel B.

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United States

We had a fantastic trip sailing around St. Martin, St. Barth and St. Kitts & Nevis with Rob and Jackie, who were super relaxed and made us feel 200% welcome. The boat is beautiful and very well taken care of, a perfect intro to real-deal sailing. Rob is an excellent skipper mindful of safety (& comfort), and Jackie spoils you with her cooking. Snorkeling gear an paddle board available for aquatic leisure. Cannot recommend them more for a relaxing trip around the Caribbean!
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BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

04/12/2025

Carla P.

-

Italy

ottimo skipper e ottimo servizio di bordo con eccellente cibo
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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.

-

Italy

Altre esperienze con voi sono state effettuate con barche più nuove e confortevoli. Suggerisco di adeguare tutte le imbarcazioni così da giustificare il costo abbastanza elevato della crociera.

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