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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?

The world's largest marketplace for sailing holidays

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

881 reviews

Four days among the islands of the Gulf of Naples

06/8/2026

Eleonora S.

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IT

For our first catamaran experience we chose Angelo and his [hidden] and we couldn't have made a better choice! A helpful and experienced captain, who made us discover the most beautiful bays of Procida and Ischia. Together with him, the cook Diego who satisfied all our requests with incredible kindness! We are super satisfied and hope to leave soon with them! [hidden] is beautiful and very well-kept, convenient even for those who, like us, had no experience of boat holidays!
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June 2 long weekend on a catamaran in the Cinque Terre

06/7/2026

LUCA M.

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IT

what can I say ... formally it was only 96 hours along the Ligurian Levante ... but on the sea time passes along like the waves and on board Cassiopeia navigation envelops you as gently as the wind towards the coast ... But what turned a long weekend into a special experience was a set of ingredients... a nice crew with intelligent children attracted more by the sea than by a tablet ... A comfortable and spacious catamaran ... but above all Antonio, a captain who makes the difference by pampering the crew, preparing delicious food and always sailing in total safety: absolutely recommended!
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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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The magic of the Egadi Islands aboard a brand new catamaran

06/1/2026

Dalia C.

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BE

Very nice skipper Alessio

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