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Holidays, Cruises, and Catamaran Trips in Italy

The unique experience of sailing on a catamaran, with its spacious layout and exceptional comfort, combined with the chance to explore Italian coasts accessible only by sea and share moments with new friends, makes every holiday unforgettable. Treat yourself to a vacation where you wake up in a bay and enjoy breakfast surrounded by the beauty of the sea.

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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.

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

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Holidays, Cruises, and Catamaran Trips in Italy

890 reviews

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North Sardinia and South Corsica by catamaran with flybridge

06/29/2026

Manoel B.

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BR

It is hard to describe the feeling about this trip. Every minute had its own unique feeling and significance. They were wonderful places for contemplation; even the silence made sense and held meaning. The boat is brand new, and despite a minor issue with the bathroom—which was quickly resolved—it exceeded my expectations. As for the sailor, Andriy: he was more than just a sailor; he was a travel companion who shared in all the special moments. We shared thoughts, silence, and moments of quiet reflection. Thank you so much for the opportunity, and remember: it is the entire crew that makes the trip what it is! Enjoy!

The magic of the Egadi Islands aboard a brand new catamaran

06/29/2026

Sara S.

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IT

New, spacious and really well maintained catamaran! It was impossible not to feel at ease also thanks to the Skipper Peppe, who immediately proved to be welcoming and super helpful! He took us to magical places, recommended unique experiences and spoiled us throughout the holiday! Super recommended experience!!
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Isole Eolie in catamarano

06/28/2026

Giuseppe G.

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IT

Antonio is a Fantastic Skipper. Super available always. Great cook and always ready to please the crew on everything. A truly exceptional person. My trip with him was unforgettable.
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Isole Eolie in catamarano

06/28/2026

Alessandro G.

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IT

A wonderful week made unique by the beauty of each island to be experienced both by sea and by land. A special thanks goes to Antonio, in addition to being an experienced and reliable skipper, he is a helpful and fun friend. He pampered us with his exquisite cuisine and always found a way to fulfill our travel wishes!

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