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Yacht sailing holidays & skippered tours in Italy

Discover more than 5 sailing holidays in Italy. Book a spot onboard and live 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 - Yacht sailing holidays & skippered tours in Italy

13613 reviews

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A week in the Aeolian Islands - 6 islands in seven days

09/15/2025

Ilaria I.

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Italy

Top experience! Nicola, the skipper, is nice and super reliable, he took us to magnificent places, he was understanding to put up with us all, always available even with the kitchen, but never intrusive, and proposed an itinerary based on the weather that allowed us to see 6 islands, and allowing those who wanted to disembark on land and take turns in the village, or stay on the boat for those who, like me, prefer to enjoy the beauty of the roadstead. Very beautiful and spacious boat, as much as a sailboat can be, equipped with many small modernity and comforts. Even the group that was created with the other participants was beautiful and cohesive, leaving everyone their own freedoms. The journey to reach the Aeolian Islands and to return, starting from Livorno, was not the easiest and most direct, but it was really worth it, so don't be discouraged but leave and choose Nicola, a man of the sea and experience, and you will feel "safe". What to add if not one I hope "see you soon!" Thank you Nicola and your [hidden]!
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A week sailing in the most beautiful places in the world

09/15/2025

Federica P.

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Italy

Nice experience with Giusy and Piero, exceptional skippers and exquisite cooks. Following the wind and currents of the period, Giusy and Piero managed to make us feel at home in their boat and make us enjoy the landscapes and the spectacular sea of Sardinia and Corsica. Two exquisite people with whom we spent a delicious week that I think we will repeat soon.
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Gaia T.

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Italy

I give two stars respectively to hostess Manuela and travel companions. For the rest, the nervousness and unjustified anxiety of the commander led to a very unpleasant situation. A lot.
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Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

09/15/2025

Nadezda O.

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Switzerland

Andrea and Calogero made our boat trip incredible and unforgettable. We met very kind Italians during this journey and, in the end, we became like a family. We celebrated my daughter's 18th birthday all together, and she was very happy to celebrate it with such a wonderful team! Each member of our team stayed until midnight so that we could open the bottle of champagne and celebrate my daughter's birthday. I really appreciate all the attention, friendship, and positive emotions we shared together. We visited many beautiful places and also tried Sardinian and Corsican restaurants. Andrea showed us and introduced us to a wild pink island, which was just a wonderland! We swam a lot :), which was marvelous. It was an extraordinary experience to see the boat flying :) with the wind and its sail open! Andrea and Calogero are great skippers! We also appreciate Sara's care and hope that we can meet her next time. Thank you for this trip! Andrea and Calogero made our boat trip incredible and unforgettable. We met very kind Italians during this trip and, in the end, we became like family. We celebrated my daughter's eighteenth birthday together, and she was very happy to celebrate it with such a wonderful team! Each member of our team stayed until midnight so we could open the bottle of champagne and celebrate my daughter's birthday. I really appreciate all the attention, friendship and positive emotions we shared together. We visited many beautiful places and also tried Sardinian restaurants and Corsicans. Andrea showed us around and introduced us to a wild pink island, which was simply a wonderland! We swam very :) which was fabulous. It was an amazing experience to see the boat fly :) with the wind and the sails open! Andrea and Calogero are great skippers! We also appreciate Sara's care and hope to meet her next time. Thank you for this trip!

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