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Yacht sailing holidays & skippered tours in Italy

Discover more than 3 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

12753 reviews

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Aeolian Islands on a luxury sailing boat

07/30/2025

valeria s.

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France

Wonderful! everything, skippers and destination. Nicoletta is always available, a competent skipper and also a good cook! Pierluigi is equally competent and passionate about this profession. They convey their passion with joy and music! To those who read, I recommend them with my eyes closed!
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Aeolian Islands - A week on a sailing boat with skipper and assistant

07/30/2025

Elisabeth G.

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France

Nice cruises almost private (4 people) so pleasant, well managed by Luigi and Erico depending on the weather and the interest of the points to see. They are professional and pleasant, give good explanations in French about places to see, restaurants, etc. Erico's cold salads are varied and pleasant considering the heat. We have good memories of it!
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Aeolian Islands on a luxury sailing boat

07/30/2025

Mirko P.

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Italy

Discover the Aeolian Islands with Pierluigi and Nicoletta aboard [hidden]. It was a unique experience. Their professionalism, sympathy, humanity and their knowledge of the islands combined with their love for the sea have meant that this holiday rightfully enters my very personal "top five" of the most beautiful holidays (even if I don't like to make rankings).
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Whale watching mini-cruise with WWF guide between Liguria and the French Riviera

07/30/2025

Ester S.

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France

Nice experience, interesting. Discovering so many new things, I would absolutely recommend it. Thank you

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