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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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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

890 reviews

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

08/4/2026

Roberta M.

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IT

It was a really nice and relaxing holiday. Rino proved to be a very professional, competent skipper and always careful to ensure safety throughout the navigation, The group was also very close-knit, helping to create a serene and fun atmosphere. An experience that I definitely recommend and that I would gladly do again.
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

08/3/2026

Bolina S.

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FR

Magnificent crew, helpful, attentive, smiling, competent, efficient, superb landscapes and unforgettable villages, unforgettable memories, thank you for any top catamaran
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Sail to the Aeolian Islands with an experienced crew on a catamaran!

08/3/2026

Roberta D.

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IT

One of the most beautiful cruises ever done! The skipper Andrea (together with the stewart Daniele) have really thought of the cruise in the best way to make us enjoy the Aeolian Islands. We toured the most beautiful coves, enjoyed fabulous meals (created with a moving attention to the quality of raw materials) on a very comfortable cat and real attention to the wishes of the guests. In short, I would leave tomorrow (but also in an hour)! Highly recommended!
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

08/2/2026

chiara p.

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IT

Wonderful experience of a week in the Aeolian Islands, all organized with care and in detail to make us live every possible experience; Angelo super helpful and nice, the wonderful boat equipped with every comfort. I also thank Giorgio so much for the impeccable skipper and Diego for a very good cook, you made us spend a wonderful week. We will definitely be back for more tours!

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