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Yacht sailing holidays & skippered tours in Italy

Discover more than 1 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

13198 reviews

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Different Flotilla: Party and new friends in the Aeolian Islands

08/23/2025

Federico F.

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Italy

Simply fantastic flotilla. Thank you all for making this holiday a wonder.
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Two days at the Marine Protected Area of the Tremiti Islands

08/23/2025

Vanessa P.

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Italy

Marco is the top! And this experience will remain forever in my heart... The sailboat makes you reconnect with yourself and with the wonderful surrounding nature. The Tremiti are wild gems. Recommended experience, Marco is a sea dog always available and kind. Rating:10
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Pontine Blue - Midweek Escape

08/23/2025

Ferdinando G.

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Italy

Perfect super skipper
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Two days at the Marine Protected Area of the Tremiti Islands

08/23/2025

Domenico P.

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Italy

Definitely recommended trip, Marco has shown to have great preparation and strong empathy. He put himself at our complete disposal to try to make us live the best possible experience. The company is also excellent and the destination is no less. however, I think it is appropriate to specify a couple of things that could help the next travelers or Marco himself in the choice to improve the experience of his next guests: The tour includes three days, but in reality, even if it is possible to embark at 16:00 on the first day, it does not leave before 9 the following morning, and we leave around 12 noon on the third day, so on the island we are in fact only 24 hours and this was not at all clear when booking. Another thing that I would like to point out (I state that it was my first experience on a sailing boat, so it could be related to my ignorance) is that the boat seemed small to accommodate eight people plus the skipper. It is difficult to relax lying in the sun with the few spaces available and the same is uncomfortable to have meals on the boat. Anyway satisfied with the experience which I highly recommend!

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