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Family sailing cruises yacht sailing holidays & tours in Italy

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

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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.

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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 - Family sailing cruises yacht sailing holidays & tours in Italy

523 reviews

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

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IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
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Aeolian Islands: between sea and authentic flavours

10/4/2026

Lorenzo F.

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IT

Fantastic experience discovering the Aeolian Islands. The holiday followed very natural rhythms in the name of relaxation. Our skipper Carlo was super! Always available and easy-going, with his great passion and professionalism he guided us to discover wonderful coves and islands. The group got along right away. Between the sea, laughter, aperitifs and crazy sunsets, it is a holiday that I would do again without thinking about it. Recommended!
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Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

09/21/2026

Gioia S.

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FR

Amazing experience ! I recommend this alternative method of holidays to everyone to have a little more awareness of the world in which we live and to continue to discover the sea.... I will definitely do it again!

Aeolian Islands: between sea and authentic flavours

09/20/2026

Manuela M.

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IT

Beautiful experience!! The skipper immediately put us at ease! Too bad it's over!!!!

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