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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

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

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 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

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

817 reviews

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The magic of the Egadi Islands aboard a brand new catamaran

10/5/2025

Marco B.

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Italy

A wonderful experience, sea, great company and fantastic food!
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/29/2025

Stella H.

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France

Fantastic destination. Great sized catamaran. Food provided by our hostess was good. There are a few of issues that need highlighting: 1. The size of the boat and its starting point changed after I booked online. 2. I had asked if a single supplement applied to my booking as (at the point of booking) the boat/catamaran only had 4 berths. I was told there wasn’t a supplement. We were assigned a larger boat and I was allotted a single cabin - the same size as for the hostess/chef. 3. I did not receive a confirmation by email of what I had booked (so had no evidence of what I was to expect when I arrived). I was in a cabin suitable for a child and had to share a bathroom. There was no WiFi available. I had no exterior window. The fan in my room only worked by connecting 2 loose wires (like hotwiring a car!). The sockets in my room worked intermittently. 4. The skipper was extremely competent in his professional work. However, his English was not good enough to be listed as a second language. In addition, he could have been more regular about informing ALL the passengers at the same time about the itinerary for the day (which differed significantly in order from that on the website). Informing us whilst we were eating would have been the perfect time. 5. On the day of departure we were asked to meet 2 hours earlier than arranged but the cleaners had not finished their work and we left 2 hours behind schedule. This we were sitting around for 4 hours unnecessarily. Better communication might have avoided this. 6. The wording for the itinerary is not clear regarding the transfer from an airport. I feel it needs to be explicit that this isn’t included. 7. The skipper was in a hurry to return to port on the night before last and omitted a final swim stop. He left the boat before the others.
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/28/2025

Sara D.

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Italy

Beyond expectations...
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Aeolian Islands - Large and new catamaran equipped with every comfort

09/28/2025

Simon F.

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Austria

Thank you maurizio and dea for making this an amazing trip Very nice islands perfect food nice boat experience

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