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Yacht sailing holidays & skippered tours in Italy

Discover more than 8 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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 - Yacht sailing holidays & skippered tours in Italy

12528 reviews

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Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

07/12/2025

Riccardo S.

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United States

Skipper Alessandro was great and the chef Mauro was amazing too! We got the left cabin in the back, which is very close to the water pump and can be annoying if you are sensitive to vibrations. AC makes a difference, I can't imagine doing something like this without it. There's space for everyone on the boat, it's similar to an RV experience but on water
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Weekend on Elba Island

07/12/2025

Roberta C.

Antony is a generous and very active person. Capable in managing the boat and a skilled and organized cook. Nice experience.!
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/12/2025

Melissa Sara C.

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Italy

Abandon yourself to the colors and flavors of the islands, the sea and the wind. The summary of a week perfectly lulled by the waves in which to breathe freedom on a perfectly maintained boat thanks to the attention that Dario the skipper gives to all things. An extremely experienced navigator, he also knows how to involve in on-board operations as well as direct to the focal points of the sea and land islands, trying to answer all my countless curiosities. For those who love sailing, top experience!
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A week in the Aeolian Islands - 6 islands in seven days

07/12/2025

Renzo G.

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Italy

We recommend a week of sun and sea with the experienced skipper Nicola. We were able to admire unspoiled landscapes, swim in the bluest sea possible and enjoy the company of a special crew!

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