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Yacht sailing holidays & skippered tours in Italy

Discover more than 7 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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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

14480 reviews

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

08/11/2026

Silvia Maria D.

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IT

Comfortable boat, very prepared skipper and assistant, super company. Too bad there wasn't so much wind
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Long weekend among the queens of the archipelago - Elba and Capraia

08/10/2026

Simone L.

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IT

Edoardo is an attentive, precise, and experienced skipper. He manages to establish an always positive atmosphere, he adapts perfectly to the spirit of the group and the will of the moment, but he manages, in his flexibility, to steer with wisdom and decision a boat that lends itself very well to the various needs of each holiday. A nice, inclusive person, and generous with explanations. Of course, the success of the holidays always depends on who you find with you, but character and skill make 90 percent of the success. When the others in the crew are also nice, easy-going and pleasant people, then fun is guaranteed.

Weekend in the Gulf of Alassio and Gallinara Island

08/10/2026

Eloisa M.

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IT

Clean sea, light days, pleasant company. The sail gave that calm rhythm that makes you feel good without the need to overdo it. Alberto organized everything impeccably, and his sailboat turned out to be really comfortable and well maintained. A peaceful weekend, made up of simple things that work.

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

08/10/2026

Paola P.

Excellent organization! Very nice skipper and prepared. Experience to be redone!!

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