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Offshore yacht sailing holidays & tours in Italy

Discover more than 4 opportunities to get on board a Offshore adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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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 - Offshore yacht sailing holidays & tours in Italy

409 reviews

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Magical sailing crossing from Procida to the Aeolian Islands

06/24/2025

Annamaria L.

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Italy

Riccardo is an experienced skipper, he loves sailing and made us experience beautiful emotions in fantastic places. He involved everyone in the management of the boat, even me who was completely inexperienced.
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Lots of sea and lots of sailing - from Corsica to Tuscany

09/12/2024

fabrizia b.

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Italy

Wonderful experience for the places visited and the great professionalism of the skipper. Ivo transmits such a love for the sea and sailing that you can't help but get involved. Intrigued by our conversation on the boat, once I returned I reread Moby Dick and there is a passage that more than any other represents the spirit and emotions that this holiday has given me: "Call me Ismaele. A few years ago - no matter how many exactly - having little or no money in my pocket and nothing particular that interested me on land, I thought of devoting myself to navigation and seeing the water part of the world. It's a way that I have to chase away melancholy and regulate circulation" Thank you f
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Catamaran immersed in the nature of Sardinia in search of well-being, from Carloforte to Cagliari

09/6/2024

Barbara T.

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Italy

Very pleasant experience, appreciated the itinerary, the comfort of the catamaran, the availability of the skipper and the volunteer cook.
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Enjoy: in the blue painted blue of the Aeolian Islands

08/20/2024

Paola T.

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Italy

The destination and the rough itinerary are beautiful (although different from the initial program despite favorable weather). The feedback, only partially sufficient, cannot be addressed to Giovanni and Matteo as they were not our skippers as we only discovered at the start. The most sore points were the capacity of the boat (too small for 10) and the distribution of cabins and bathrooms (not allocated equally). But above all, the departure delayed by a day due to a refrigerator breakdown (obviously not attributable to the skippers) which resulted in an unpleasant night in port lost compared to the initial program. We recommend defining these aspects independently and in advance as well as the organization of activities on the islands, as the organization of skippers is partial and often oriented towards overly touristy solutions. From a human point of view, it is an experience that we absolutely recommend, we found wonderful people and the weather on the boat was beautiful.

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