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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.

Why book a holiday with Sailsquare?

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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.

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

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 - Holidays, Cruises, and Catamaran Trips in Italy

1066 reviews

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Weekend catamaran in Portovenere and Cinque Terre

09/29/2026

Coretta P.

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IT

Antonio proved to be a very knowledgeable, organized, helpful and patient owner/skipper. The catamaran was found to be particularly comfortable and well maintained. Splendid itinerary and the weather also favored us. In short, a beautiful weekend!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

09/29/2026

Sergio V.

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IT

Alessandro is first of all a great person, then as far as the week is concerned he proved to be available and attentive to the requests and desires of the crew, precious for suggestions and advice on what to do. He always accompanied us even on the ground. Helena, passionate about her work, has always prepared different dishes that are satisfying for the taste and for the eyes. It couldn't have been better than this!

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/29/2026

Gloris M.

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IT

We had a wonderful week. The skipper Fabrizio, always very kind, made us feel safe with great professionalism and tried to satisfy all our requests compatibly with the weather. The hostess Monica, always discreet and patient, knew how to take care of the guests without being intrusive. He prepared tasty dishes that helped make the holiday even more enjoyable. If we could we would leave immediately for another holiday with this crew!

Weekend catamaran in Portovenere and Cinque Terre

09/29/2026

Chiara M.

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IT

Super pleasant weekend, nice company and attentive and very well organized skipper. I would leave tomorrow🫶🏻

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