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Yacht sailing holidays & skippered tours in Italy

Discover more than 6 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

6

experiences

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

2998 reviews

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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

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Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..
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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

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Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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Elba... the scents, the sea and its colors!

10/9/2023

Lucia I.

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Italy

Ivo molto bravo e professionale .beliissima esperienza
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Long weekend of sailing and trekking on the Island of Elba - 2 boats

10/6/2023

Roberta M.

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Italy

Bellissima esperienza, bellissimo equipaggio, ma soprattutto ottimo Skipper!!! Marco mette a suo agio le persone, sempre disponibile e molto preparato. Mi ha permesso di affrontare serenamente la mia prima esperienza in barca a vela. Visitando nuovi posti grazie anche alla perfetta combinazione barca a vela + trekking (e ben organizzata, un ringraziamento anche Francesco "Checco" la nostra guida!) Grazie a tutto il meraviglioso gruppo che mi ha accompagnato in questa nuova avventura!!!

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