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Monohull yacht sailing holidays & tours in the Grenadines

Discover the magic of sailing holidays in the Grenadines! Monohull: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

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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 - Monohull yacht sailing holidays & tours in the Grenadines

53 reviews

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Sailing adventure through the Caribbean: St Vincent & the Grenadines

02/8/2025

mara v.

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Italy

Adventure aboard a wonderful ketch, the skipper Hernan a person of absolute professionalism, competence and with great experience in the world of navigation led us to discover fantastic glimpses of paradise in the Caribbean. It was a good experience from every point of view. Very competitive price of the trip and boat equipped with everything. I would definitely rely on skipper Hernan again for another adventure aboard [hidden]
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New Year's Eve under the Caribbean sun

01/14/2025

Gaetano F.

I had wanted to sail to the Grenadines for a long time. I am overall quite satisfied with the holiday, despite a bit of tension between a crew member and the captain
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Sailing course in the Grenadines

03/31/2022

Sandra K.

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United Kingdom

I guess the communication was the biggest issue, despite speaking some English relaying information back was poorly executed by the skipper, which have cost me my flight, some lack of empathy during hiking trips instead of allowing time to rest he was pushing for faster or take the bus. Speaking French round the table despite 2 people not speaking the language out of 4 was little rude, otherwise he was very caring when I was unwell during sailing at times and provided effective medical solution, The trip however was a blast, beautiful islands and locals with packed activities, and amazing memories to remember. ---------------------- SKIPPER ------------------------------ Hello Sandra, I'm really sorry that the cruise you booked didn't live up to your expectations. I did everything I could to create a good atmosphere on board, even with a mixed crew speaking different languages. The holidays you booked were a sailing course where you had to travel several kilometers. My goal was to transmit the passion and rudiments of sailing. For an itinerary that includes the Grenadines Islands, there are many hours to devote to navigation.
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Christmas in the Caribbean ... a dream called the Grenadines

12/9/2020

Fabian M.

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St. Martin

Michele is an excellent skipper -- technically sound, mature and responsible -- and an excellent host on board. He is also delightful company. I recommend him without qualification

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