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Flotilla yacht sailing holidays & tours in Caribbean

Discover more than 1 opportunities to get on board a Flotilla adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

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experience

Why book a holiday with Sailsquare?

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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 - Flotilla yacht sailing holidays & tours in Caribbean

50 reviews

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New Year's Eve Cruise to the Grenadine Islands - LAST PLACE WOMEN

01/11/2023

Alessandro C.

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Italy

Grande Andrea, la vacanza è stata stupenda anche per merito suo. Mi son sentito sempre al sicuro grazie alla sua esperienza di navigazione ed è riuscito a tenere barca ed equipaggio in forma con discrezione.
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New Year's Eve Cruise to the Grenadine Islands - LAST PLACE WOMEN

01/9/2023

David H.

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United States

Unfortunately I didn't get to sail with Andrea because I got sick at the last minute but his communications with me were superlative throughout and I have followed the holiday on whatsapp and can tell from the photos and videos that he did a great job, the holiday was outstanding, I greatly regret not being able to attend and hope to go on one with Andrea in the future.
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Discovering the Grenadines by catamaran

01/13/2020

SIMONE P.

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Italy

Massimo è uno Skipper speciale, un ragazzo che ama il mare prima di tutto, naviga con il sorriso e la giusta concentrazione, è preparato tecnicamente e mantiene la giusta calma in ogni situazione. Una volta ormeggiata la barca in sicurezza non manca il suo coinvolgimento con il gruppo per fare festa e divertirsi, inoltre è sempre disponibile verso le esigenze di tutti, e come dice lui "con calma!". TOP SKIPPER !!!
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New Year's Flotilla - 2 Catamarans in the Grenadines

01/11/2020

Pierpaolo F.

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Switzerland

Buon marinaio e velista.

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