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Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 7 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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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 - Family sailing cruises yacht sailing holidays & tours in Italy

349 reviews

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Weekend on a sailing boat between Capraia and Elba

09/15/2025

Tamara V.

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Italy

Nice very new boat but some amenities were missing. I thought better destinations Good skipper
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Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

09/15/2025

Patrik D.

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Germany

The one week on the boat "[hidden]" with Skipper Paolo and Sailor Vitorrio was absolutly amazing and passed way too fast. Paolo is a really good skipper who knows the best spots, best bays and best restaurants all while explaining and teaching you about sailing. Vitorrio is a superb sailor, always helpfull and upbeat, excellent cook and perfect apnea buddy. The north coast of Sardegna and southcoast of Corsica hold pristine beaches, amazing sunsets and delicious food and life on board feels like class trip with only the best things of it. Can recommend it sincerly to everybody, no matter age or origin, just go and do it and see for yourself!
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Capri LightBlue and Positano BluSKy

09/14/2025

Maurizio G.

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Italy

Everything went well prepared skipper helpful and nice beautiful Capri beautiful
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

09/14/2025

Sophie F.

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United States

A fantastic week sailing with a wonderful group. The boat is very spacious and there is enough room for people to have their own privacy. The cabins even have air-conditioning, which we didn't need but could be useful during a heatwave. Luca and Tomasso were great hosts, super friendly and happy for us to help with the sailing or just relax. The company of the other guests was fantastic. The scenery is incredibly beautiful. 4 stars instead of 5 because the food was OK but not great, and not super healthy. Essentially only lunch and dinner are included. Breakfast is coffee and a bag of store-bought cookies and crackers. Tons of white carbs for meals and snacks. There were very few vegetables (lunch salads were iceberg lettuce in a package that said 99 cents), a shame in the Mediterranean, especially in summer. Another downside was that, on the last day, we came back to the port quite early so our afternoon at sea was cut short, so this was really 5.5 days.

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