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Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 8 opportunities to get on board a Family sailing cruises adventure in Italy. 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 - Family sailing cruises yacht sailing holidays & tours in Italy

369 reviews

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Poetic Gulf of Poets

10/9/2025

Massimo G.

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Italy

Giovanni is a professional at his job,.. Expert, and collaborative with his customers... ADVICE....
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Poetic Gulf of Poets

10/6/2025

Fabiola R.

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Italy

Beautiful experience!! Giovanni is a wonderful person and d a prepared skipper, the itinerary is lovely .... definitely try
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Poetic Gulf of Poets

10/6/2025

Domenico C.

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Italy

Giovanni is an attentive skipper, very competent and extremely helpful. I recommend it!
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Long weekend of whale watching with WWF guide on an 18-meter schooner

10/2/2025

Marco C.

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Italy

Unforgettable experience aboard the Schooner Mahayana. An essential and shared life on board. Thanks to Captain Francesco, his crew and WWF guide Ilaria, a serene and pleasant atmosphere was established with all guests from the beginning. Browsing great places. Educational experience on the marine environment with a focus on cetaceans and environmental impact. As a first experience we particularly appreciated the pace of navigation, the life on board and the company.

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