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Yacht sailing holidays & skippered tours in Italy

Discover more than 2 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

13626 reviews

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Long weekend of whale watching with WWF guide on an 18-meter schooner

09/16/2025

Paolo S.

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Italy

Wonderful experience
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Capri LightBlue and Positano BluSKy

09/16/2025

Claudia D.

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Italy

We have just returned from a beautiful holiday that allowed us to visit wonderful places with a convenient and comfortable boat; Gennaro, was a skipper who was always friendly and attentive to all our needs, he showed great ability and experience even in solving small unforeseen events; definitely to be repeated!!
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

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Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/16/2025

Renate D.

-

Italy

Stefano is a pleasant, discreet and balanced person. You have a great sense of security and manage a beautiful boat - where nothing is missing - in an exemplary way, it seems that everything is simple! The tour he offers is dreamlike, every five minutes you find yourself saying "How beautiful!", A magical experience with a confident and very competent person both in practical management and on a relational level.

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