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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 8 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

4 departures available

October - November

Starting from

€1,680

€1,512

Per person - min 2 pax

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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

4 departures available

October - November

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

October - November

Starting from

€1,250

€1,125

Per person

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4.3

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

2 departures available

October - November

Starting from

€1,125

€1,013

Per person

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4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

2 departures available

October - November

Starting from

€1,125

€1,013

Per person

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4.3

Premium

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

Caribbean: Bahamas

6 days - 7 nights

One departure available

October - November

Starting from

€1,865

Per person

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South Carribean - Dream cruise with skipper/cook

Caribbean: Trinidad and Tobago

14 days - 14 nights

One departure available

October

€2,300

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

5 departures available

September - November

Starting from

€1,350

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

219 reviews

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

06/30/2025

Beatrice S.

-

Spain

You couldn't expect more than one trip. The big new catamaran. A/C whenever needed and plenty of water. Captain Lutius could not be more professional and friendly. He made us all feel comfortable and always proposing to do different activities in a fun and casual atmosphere. Karin, the chef equally nice and funny. Very professional and attentive to our needs. The places we visited in a dream and despite some rains in general have been worth sailing out of season as we are practically alone in the most amazing places. We have always been lucky with the rest of the clients and in this case it has not been different and despite being mostly French-speaking we have communicated very well in English.
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12 day Cruising/Sailing Experience around St. Martin and St. Barth's

04/17/2025

Basiel B.

-

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.

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Italy

Great skipper and great service on board with excellent food
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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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