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Yacht sailing holidays & skippered tours in Italy

Discover more than 9 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.

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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

13898 reviews

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Midweek relaxing in the Pontine Islands

06/15/2026

Andrea G.

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IT

Experience to frame! Mirko is a very prepared and helpful skipper, as well as a wonderful person and an excellent cook. The boat is large and equipped with every comfort and convenience. The scenery of the Pontine made everything superlative and unforgettable. SUPER RECOMMENDED!!

Midweek relaxing in the Pontine Islands

06/15/2026

Emanuele S.

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IT

I would say everything perfect! Starting with the boat which is almost new, clean and efficient! Then special mention for the skipper Mirko who, in addition to being an excellent captain, is at the same time a cook, tour guide, entertainer, barman ... etc etc . super recommended holiday ! Fair winds to all !!

Dream weekend in the Pontine Islands

06/15/2026

Federico F.

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IT

Beautiful experience! Breathtaking landscapes and crystal clear sea. Stefano, an expert commander, cheered us up during the day allowing us to sail and collaborate in maneuvers, and in the evening with guitar and songs in the moonlight; Francesca, the perfect hostess, pampered us by cooking delicacies and never letting us miss anything. When we spoke to her for the first time, she immediately made us feel welcomed, and so it was. The boat is comfortable and well maintained. In addition, the luck of having met sociable and expansive people on board made everything perfect. Highly recommended
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Weekend among the most beautiful coves of Elba

06/14/2026

Roberto L.

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IT

Thanks to Marco and Carmen for the wonderful weekend they made us spend on the fantastic island of Elba. Three days full of laughter and lightheartedness ... Keep up the good work

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