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Offshore yacht sailing holidays & tours in Italy

Discover more than 1 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

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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

411 reviews

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Travel to Sardinia: from South to North

09/7/2025

Veronica C.

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Italy

It was a unique experience! First time on a boat for so long such a long stretch. (South-North). I confirm what I read in the reviews! The crew made us feel like family! Leo is a very experienced skipper who handles all types of wind and sea and makes you feel safe at all times ... And what about lunches and aperitifs (essential Ale and Luis)! Unique! Also an excellent choice of beaches where you can stop for swimming and relaxing! I will definitely do another experience with them in other places!
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From Alghero to Carloforte and Teulada discover the west coast of Sardinia

08/17/2025

Alice S.

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Italy

Federico is the king of skippers, he takes care of his boat [hidden] like a jewel and passed on his passion for sailing, fabulous destinations along the west coast of Sardinia, Thank you for the wonderful experience.
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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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