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Courses & regatta yacht sailing holidays & tours in Italy

Discover more than 3 opportunities to get on board a Courses & regatta adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

3

experiences

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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 - Courses & regatta yacht sailing holidays & tours in Italy

514 reviews

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From the AEOLIAN to the PONTINE - Adventure, Navigation and Relaxation - One Way

09/29/2023

Maya P.

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Italy

Professionalità simpatia serietà ma soprattutto un insegnante fantastico: chiarezza, disponibilità, e conoscenza trasmesse in ogni istante con spontanea semplicità con al primo posto sempre la sicurezza di tutti. Grazie cercavo una vacanza scuola me la immaginavo proprio così. Oggi mi porto a casa molte nozioni interessanti che non vedo l’ora di mettere in pratica di nuovo e approfondire, ma anche tanto relax e un soffio di vento nei capelli ??????????????????????
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Two boats together - Sailing on the island of Elba! Between the sea, courses and new friends... you forget everything! :-)

09/29/2023

Italy B.

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Italy

Questa vacanza con Luca ha rispettato le aspettative. Luca è molto disponibile anche ad accomodare eventuali necessità. La vacanza è stata divertente e con possibilità di timonare ed apprendere nuove conoscenze riguardo la navigazione.
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Alghero to the Costa Smeralda

09/26/2023

Bruno T.

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France

Nous avons passé une très bonne semaine avec Tommaso sur son beau voilier. Le temps n'a pas toujours été idéal pour la navigation, et le programme n'a pas pu être réalisé, mais notre skipper nous a trouvé des visites, des restaurants et des balades sympathiques pour nous consoler. Nous avons découvert la vie à bord et appris la conduite du bateau. Dommage pour la Maddalena, nous n'avons plus qu'à recommencer. Avec Tommaso peut être !
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Free in the Wind!... perfumes and wonders in the upper Adriatic

09/25/2023

Enzo B.

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Italy

Ottimo skipper ma soprattutto bella persona; è stato un piacere passare una giornata in barca a vela con Paolo. Anche per le persone alle primissime armi è un tipo di esperienza super consigliata avendo la certezza che Paolo vi aiuterà a vivere al meglio questa diversa dimensione del mare. Buona navigazione a TUTTI

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