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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 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Caribbean: Grenadines & Martinique

9 days - 10 nights

3 departures available

August - September

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

4 departures available

August

Starting from

€1,125

€1,013

Per person

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4.3

Premium

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

Caribbean: Grenadines & Martinique

6 days - 7 nights

5 departures available

August - September

Starting from

€1,250

€1,125

Per person

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4.3

Premium

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

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

2 departures available

August

Starting from

€1,250

€1,125

Per person

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4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

3 departures available

August

Starting from

€1,125

€1,013

Per person

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5.0

San Blas Islands - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

One departure available

August

€1,167

Per person

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5.0

San Blas Islands: Private Boat for 2 Persons - All Inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

One departure available

August - September

Starting from

€1,625

Per person

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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

August - September

Starting from

€1,350

Per person

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5.0

Sailing and Wild Life in San Blas between traditions and turquoise waters

Caribbean: San Blas Islands - Panama

7 days - 7 nights

3 departures available

August - September

Starting from

€1,500

€1,350

Per person

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Explore San Blas paradise

Caribbean: San Blas Islands - Panama

4 days - 4 nights

5 departures available

August - September

€200

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

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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