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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

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

2 departures available

January - March

€850

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

3 departures available

February - December

€730

Per person

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4.3

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

52 departures available

January - December

Starting from

€1,250

€1,125

Per person

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5.0

Super!

Thailand and the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

One departure available

December

€1,450

€1,378

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Malé to Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

Per person

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5.0

Super!

Seyschelles Islands... Welcome to paradise!

Indian Ocean: Seychelles

11 days - 11 nights

3 departures available

April - June

Starting from

€2,400

€2,040

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Kulhudhuffushi to Malé

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February - March

€2,650

Per person

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4.3

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

34 departures available

January - December

Starting from

€1,680

€1,512

Per person - min 2 pax

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5.0

Grenadines Islands in winter: Christmas on a catamaran

Caribbean: Grenadines & Martinique

11 days - 11 nights

One departure available

December

€1,559

Per person

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

18 departures available

January - December

Starting from

€1,272

Per person - min 2 pax

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4.3

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

23 departures available

January - December

Starting from

€2,330

€2,097

Per person - min 2 pax

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4.9

Under the Caribbean sun on a catamaran

Caribbean: Grenadines & Martinique

8 days - 9 nights

2 departures available

February - March

€1,750

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

71 reviews

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GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

10/28/2025

Anne-Marie G.

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Curaçao

Amazing experience
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From the Fiji Islands to New Zealand: a unique adventure

10/4/2025

Christoph M.

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Germany

It was a wonderful sailing trip. Francesco was not only a great skipper but also a great cook. We had all the combinations of wind and weather, but under the guidance of the skipper you always felt safe. Thank you for the great trip to New Zealand. Christoph
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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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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

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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