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Sailing Holidays and Catamaran Cruises to Exotic Destinations

Hidden lagoons, unnamed islands, and skies without borders: your adventure of nature, wonder, and freedom begins where the maps end. Sail through remote atolls, coral reefs, and palm trees brushing the ocean. Dive into crystal-clear waters teeming with colorful fish, explore deserted beaches, and listen to the silence of the tropics under the stars. Every bay is a new marvel. Every day, a new adventure in a dreamlike setting.

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4.8

Venez découvrir la Guadeloupe et son archipel: un paradis sur l'eau

Caribbean: Guadeloupe

7 days - 7 nights

11 departures available

January - December

€850

Per person

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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

42 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

64 departures available

January - December

Starting from

€1,250

€1,125

Per person

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4.3

Premium

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

Indian Ocean: Seychelles

7 days - 7 nights

63 departures available

January - December

Starting from

€1,760

€1,584

Per person

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4.9

Under the Caribbean Sun

Caribbean: Antigua and Barbuda

8 days - 9 nights

One departure available

December - January

€2,200

€2,000

Per person

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4.9

Under the Caribbean sun on a catamaran

Caribbean: Grenadines & Martinique

8 days - 9 nights

3 departures available

January - March

€1,750

Per person

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5.0

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

3 departures available

December

€1,450

€1,378

Per person

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

€3,000

€2,100

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

51 departures available

January - December

Starting from

€1,125

€1,013

Per person

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5.0

Maldive da sogno in barca a vela - Da Malé a Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

€2,253

Per person

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4.5

Paradise Seychelles by sailing catamaran

Indian Ocean: Seychelles

7 days - 7 nights

2 departures available

November - December

€1,450

Per person

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4.8

Venez découvrir la Guadeloupe et son archipel: un paradis sur l'eau

Caribbean: Guadeloupe

6 days - 6 nights

3 departures available

February - March

€730

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 - Sailing Holidays and Catamaran Cruises to Exotic Destinations

69 reviews

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Discovering the Fiji Islands: a paradise on earth

09/8/2025

Sara R.

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Italy

We thank Anna and Ghego for the absolutely great time. Lots of adventure in the water and on land. The food was really good. Anna and Ghego are very welcoming and easy going, we loved our time on the Mezar :) Ghego is a very skilled sailor and Anna with her artist side add a magical touch to the experience.
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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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PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

05/9/2025

Sara Angela R.

I went on a catamaran cruise with a skipper and cook, but unfortunately the experience did not live up to expectations. The destination and the proposed itinerary are truly splendid, as well as the cuisine on board, which was a highlight. The model of the boat is also very appealing, but the boat was not in optimal condition: the air conditioning worked intermittently, there was water seepage in the cabin, and overall it did not offer the promised level of comfort and luxury. The crew, especially the skipper, was cold and uncommunicative, to the point that explaining the stages or simply asking him a question seemed almost a disturbance. This made the experience on board rather flat and unengaging. In summary, despite the beauty of the places visited and the good food, the service and condition of the boat do not justify the price paid. Disappointing value for money.
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Seychelles paradise by Catamaran

05/6/2025

Fabrizio P.

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Italy

a week on a catamaran in the Seychelles with an Italian crew is pure magic. Ciccio the captain Peppe vice-captain and Claudia the cook. Impeccable hospitality, turquoise sea and postcard beaches. Guests toooooopppppp.

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