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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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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

13883 reviews

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Summer is made for the Aeolian Islands! Weekly cruise

06/11/2026

Patrizia R.

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IT

Very comfortable boat. For the first time I found a skipper who lent himself to the purchase of a galley without waste and in any case complete and integrated by specific requests of the crew. The skipper also prepared tasty meals on board, including typical dishes of the Aeolian culinary tradition. On board we enjoyed a relaxed and very pleasant atmosphere and the stops took place, weather permitting, in the most iconic places of the Aeolian archipelago. It is an experience that I certainly recommend. Patricia

June 2 - cetacean watching expedition in the Pelagos Sanctuary with WWF guide

06/10/2026

Guido F.

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IT

Beautiful experience. The enthusiasm and ability to involve biologists is remarkable. The only pity we never sailed.

Weekend in Ischia and Ventotene: History and Nature

06/10/2026

Michele F.

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IT

Wonderful holiday! The boat was very comfortable, spacious and always spotlessly clean. A special thanks to Umberto, skipper par excellence: excellent sailor, profound connoisseur of the places visited and always ready to share curiosities and advice. Always available, professional and super nice, he made the experience even more enjoyable. Highly recommended for those who want to experience a relaxing and fun boat holiday with an excellent selection of music!

June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene

06/10/2026

Donatella L.

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IT

Extraordinary, welcoming skippers and also creative cooks! Highly recommended!

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