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Catamaran yacht sailing holidays & tours in the Caribbean

Get on board on your dream catamaran cruise in the Caribbean! Travel in comfort with your partner, friends or family to discover Cuba, the Bahamas, the Grenadines, Guadeloupe and the Virgin Islands.

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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

52 departures available

January - December

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

74 departures available

January - December

Starting from

€1,250

€1,125

Per person

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4.9

Under the Caribbean sun on a catamaran

Caribbean: Grenadines & Martinique

8 days - 9 nights

4 departures available

January - March

€1,750

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

53 departures available

January - December

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

57 departures available

January - December

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

55 departures available

January - December

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

8 departures available

July - December

Starting from

€1,865

Per person

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

21 departures available

January - December

Starting from

€1,272

Per person - min 2 pax

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4.9

Under the Caribbean Sun

Caribbean: Antigua and Barbuda

10 days - 11 nights

One departure available

December - January

€2,200

Per person

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4.3

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

2 departures available

January

Starting from

€2,490

Per person - min 2 pax

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4.3

Premium

ABACO Dream Premium - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

7 days - 7 nights

37 departures available

January - December

Starting from

€1,885

€1,697

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 - Catamaran yacht sailing holidays & tours in the Caribbean

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

04/12/2025

Carla P.

-

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

02/24/2025

Stefania T.

-

Italy

Other experiences with you have been made with newer and more comfortable boats. I suggest adapting all the boats so as to justify the fairly high cost of the cruise.

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