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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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Reviews - Yacht sailing holidays & skippered tours in Italy

13842 reviews

Pontine Islands in 4 days: sailing, caves and crystal clear waters

06/4/2026

Matteo B.

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IT

The boat was really comfortable, with ample space and private bathroom for each cabin. The downside is that the mainsail was a bit battered and the boat setting was not optimized for sailing. The skipper, Dario, is truly a character with endless stories that will keep you company throughout the trip. If you are lucky, like me, to find fantastic travel companions, you can only enjoy the wonderful Pontine islands!

Long weekend of June 2nd on the Costa Smeralda

06/4/2026

Silvia B.

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IT

Francesco guided us in the world of relaxation and zero stress, lulled by the sea, following the rhythm of the sun and the delicious dinners prepared by him, transmitting his love for sailing and for [hidden]. Removed the watch and forgotten the cell phone, the only commitments are swimming, balancing on. Sup, prepare loaded spritzes and exchange jokes and life anecdotes with those who become your roommates (in this case excellent) for a few days. Thank you Francesco and thank you crew!

June 2nd long weekend: discovering Capri, Ischia and Procida

06/4/2026

Ivana G.

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IT

Very comfortable, spacious and clean sailboat. Gennaro proved to be a nice and helpful skipper, helping to make the experience on board pleasant, and also participating in land trips. Less convincing, however, was the management of the itinerary: the moorings were often far from the coast, even with favorable weather conditions, and the stops did not allow you to explore exclusive places that could only be reached by sea. Furthermore, despite being part of the program, the tender was never used, limiting the possibilities of visiting coves and more hidden areas. Overall, a relaxing and pleasant experience, but below expectations in terms of exploration and itinerary, considering that the context would have allowed it.

June 2 long weekend between Capraia and Corsica - 2 boats

06/4/2026

Rebecca C.

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IT

It was a beautiful holiday, we sailed between Elba and Capraia and both Matteo and Alessio (the skippers of the two boats) were impeccable, really good and professional. On board I found a wonderful company that made these 4 days truly unforgettable! Super recommended experience

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