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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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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

99 reviews

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Sail with us in the heart of the Paradise called the Grenadines

04/30/2024

Paolo G.

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Italy

Grazie Luca per questa esperienza indimenticabile! Essere a bordo di Ikigai ci ha fatto capire la vostra filosofia di viaggio e di vita, un'avventura unica che ci ha fatto sentire fra amici e non semplici ospiti o turisti..i posti visti sono incredibili ma il mood respirato a bordo, le attività e il cibo preparato da voi rimarranno scolpiti nella memoria...speriamo di rivederevi e tornare presto a bordo...buon vento!
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

02/5/2024

MARIO I.

when I made the reservation I paid for a superior cabin and with the specific request written to you to have a bow cabin. I was assigned a central cabin, I would have liked an official communication from you, informing me of the availability or otherwise of the forward cabin and leaving me the free will to decide whether to accept or not, or withdraw from the contract for which I had paid. commercial and communication incorrectness
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From Martinique to the discovery of the Grenadines on a luxury catamaran

02/5/2024

Alessia P.

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Italy

L'esperienza con lo skipper Alessandro e' stata davvero piacevole. Un itinerario ampio e variegato alla scoperta delle bellezze dei caraibi. Alessandro e' una persona sempre disponibile, accogliente e cordiale con tutti. Il clima con il resto del gruppo armonioso e divertente. Siamo stati un po' sfortunati con il tempo ma non ci siamo scoraggiati e siamo stati ripagati dalla vista di meravigliosi arcobaleni e addirittura da un gruppo di balenotteri che ci ha accompagnato durante un tratto della nostra traversata.
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GRENADINE 11 giorni in catamarano ALL INCLUSIVE con hostess/cuoco

05/7/2023

Rob H.

Stunning trip - wonderful deserted beaches, incredible snorkling (though sad that the coral is so depleted), and delicious food. Skipper was Eric and Yuna i.c. the kitchen.

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