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Yacht sailing holidays & skippered tours in Italy

Discover more than 2 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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 - Yacht sailing holidays & skippered tours in Italy

13644 reviews

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Summer is made for the Aeolian Islands! Weekly cruise

09/18/2025

Jurij P.

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Italy

Nothing to complain about the Skipper, the destination and the boat... Since Davide, proved to be a person with great experience very attentive to the needs of each participant in the experience... And even his boat, which I had chosen because it was equipped with a bathroom for each cabin, proved to be what was expected... The same thing is the itinerary which of course can also depend on the weather accounts, which Davide has been able to manage very well ... Unfortunately, however, this time the sore point is related to the fact that I was able to see a huge flaw not in the boat but in what is the transparency policy of this site ... Unfortunately, in fact, sure that I have PURPOSELY booked an experience with all my peers - upon arrival I discover that unlike what had prompted me to make the reservation with this search engine wandering € 150 more than the other participants all ... In addition to the insurance another € 90 - on arrival then at boarding I discover that unlike this there were four over sixty years old ... As well as two girls about 20 years younger than me... This situation, even if I was able to meet and discover people of great depth and moral qualities, was not at all relevant to what I believed to be the holiday really booked... And this is simply because, with people of more or less twenty years of difference, life habits and therefore also those of a holiday, can result in diametrically opposed needs in terms of schedules and style of holiday... This I repeat Without taking anything away from the goodness of the people I know... I AM THEREFORE SORRY TO HAVE TO REVIEW THIS EXPERIENCE IN A VERY NEGATIVE WAY BECAUSE IN MY OPINION IT IS THE PORTAL OR THE ENGINE RESPONSIBLE FOR THE LACK OF TRANSPARENCY THAT INSTEAD DE' SINGS SO MUCH ON ITS SITE PRECISELY BECAUSE OF ITS AGE. FROM NOW ON AND ESPECIALLY IF THIS POLICY IS NOT REALLY CORRECTED, I WILL DO LIKE MANY BY LOOKING FOR AND CONTACTING THE SKIPPERS DIRECTLY, SINCE I WAS NOT AT ALL SATISFIED WITH THE POLICY OF TRANSPARENCY FEARED BUT NOT REALLY PRACTICED. It should therefore be noted that although I gave full marks to both Skipper Davide and the destination as well as his boat, the overall grade of the experience can only be at a minimum due only to the lack of IMPLEMENTATION of transparency, FEARED on this portal. You are curious whether or not this will be published and made available for reading by all greetings without thanks. Yuri
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Midweek special on the island of Elba, 2 nights

09/18/2025

Roberta Anna P.

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Italy

First experience on a boat. I can say that thanks to Marco, his competence and his kindness, I loved this experience from the first to the last second and it made me want to start again immediately, indeed, never to go down again. Thank you Marco.
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Relaxing weekend between Portovenere and the 5 Terre

09/18/2025

Silvia I.

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Italy

First experience on a sailing boat and it was very nice. Pleasant company and comfortable boat. Too bad for the weather that did not allow us to visit the Cinque Terre, we could certainly have been luckier! I recommend it.
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/17/2025

Mauro Z.

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Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda

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