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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.

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

13203 reviews

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Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

08/23/2025

ANDREA L.

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Italy

Wonderful holiday on board a Lagoon 50 (practically new) that offers ample comfortable spaces to enjoy relaxing days and moments of navigation in the best possible way. The skipper Maurizio, very competent and professional, was able to manage the boat in the best possible way, transmitting safety both during navigation and during mooring maneuvers! He is also willing to teach the rudiments of the trade to those who, like me, are interested in learning them. Finally, congratulations must also be made to Rachele, the hostess, who prepared excellent meals for us and was able to bond well with the group! Until next time! Andrea and Federica
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/23/2025

Andrea M.

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Italy

Nice experience overall. Tour with beautiful locations and good management by the organizers. The coexistence with other people was interesting and the natural places we visited were suggestive. Thank you and see you next time!
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Sailing & adventure in the Aeolian Islands

08/23/2025

Marta M.

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Italy

The week was wonderful, the Aeolian Islands are a place full of magic and experiencing them from the sea amplifies the suggestion. Vittorio is a true attentive and scrupulous professional, you can feel the deep bond he has with the sea and his boat. Always available to take us and retrieve us anywhere. We all felt at home and he didn't miss anything. Thank you To be repeated asap❣️
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Three days at the Marine Protected Area of the Tremiti Islands

08/23/2025

Stefano S.

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Italy

Excellent mini cruise spent in excellent company and well managed by the good Marco

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