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Yacht sailing holidays & skippered tours in Italy

Discover more than 8 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

12350 reviews

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Pontine Islands aboard a splendid 16-meter sailboat

06/20/2025

Francesco V.

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Italy

Esperienza fantastica, ben organizzata. Sono veramente soddisfatto dell'itinerario e dell'equipaggio che si è creato. Coppia Skipper bellissima e super disponibile
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Weekend of relaxation and fun from Genoa

06/20/2025

Cristina B.

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Italy

Come prima esperienza in barca a vela direi super positiva
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Sailing weekend in Liguria

06/18/2025

Giampietro D.

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Italy

Barca confortevole, pulita e in ottime condizioni. Ottimo weekend anche se le condizioni meteo non erano delle migliori ed Alessandro ha sempre gestito ogni manovra con grande destrezza e sicurezza oltre a regalare momenti di ottima compagnia e simpatia. Consigliatissimo!!!
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Aeolian Islands - Large and new catamaran equipped with every comfort

06/18/2025

Anton R.

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Germany

Very nice boat, comfortable, own bathroom, nice bath. The islands, Volcano hike, Stromboli Lava seeing at night and the Island villages are all very beautiful. Maurizio is a nice, relaxed skipper. Can definitely recommend :)

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