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Yacht sailing holidays & skippered tours in Italy

Discover more than 1 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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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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Reviews - Yacht sailing holidays & skippered tours in Italy

13822 reviews

Weekend among the most beautiful coves of Elba

06/2/2026

Annalisa D.

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IT

It was a beautiful experience. Marco and Carmen guided us and accompanied us on a wonderful journey. The luck of meeting a group of beautiful people made everything much easier and even the small difficulties were overcome with ease. This time I think I can really say...... FAIR WINDS TO ALL!!!!
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The magic of the Egadi Islands aboard a brand new catamaran

06/2/2026

Kris D.

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BE

Amazing islands, flexible chartered, professional skipper.
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Gulf of Poets

06/2/2026

Flavia B.

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IT

Giovanni is the most beautiful discovery of this trip. After so many bad experiences, finally a person attentive to the needs of the crew, reserved but at the same time open and welcoming. Thanks to him we discovered magnificent coves, stories and magical places. We will definitely be back!
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Weekend among the most beautiful coves of Elba

06/2/2026

Gianmario B.

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IT

We spent the weekend with two professional, attentive and caring people towards guests. Carmen and Marco are people who enter into symbiosis right away, giving full availability to make you feel at ease and as if you have always known them. Boat in excellent condition, nothing is missing, you obviously need a spirit of adaptation not being in your bathroom at home. The relationship that is created during the experience with all the guests is also beautiful, in this experience we met wonderful people. We recommend everyone and Fair Winds

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