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Sailboat yacht sailing holidays & tours in Sicily

Discover more than 11 opportunities to get on board a Sailboat adventure in Sicily. 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 - Sailboat yacht sailing holidays & tours in Sicily

33 reviews

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Crossing to the northwest: sailing weekend in Sicily

06/6/2025

Lisa N.

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Italy

Weekend di fine maggio proprio bello con Antonio e Bianca! Tutto è stato perfetto, dalla loro grande esperienza in mare alla gentilezza e all’atmosfera di famiglia. La barca è un gioiellino, tenuto con cura e amore. Loro due veri amanti del mare, con tantissima esperienza. Assolutamente raccomandati 🥰
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Mini cruise Syracuse - Marzamemi with hostess and galley included

09/30/2024

Francesco C.

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Italy

Capitano e hostess fantastici! Una bellissima avventura immersiva nel mare e nel sole!
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COUS COUS FEST: A Long Week End of Sea, Sailing and Cous Cous!

09/24/2023

Afshin T.

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United States

Davide was a fantastic skipper. He made sure we are all comfortable and safe during our sailing. He went out of his way to make this trip an amazing experience for all of us on board. It was such a fun adventurous time sailing on Davide’s boat, and also off the boart while on port enjoying the cous cous festival, bbq and partying.
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COUS COUS FEST: A Long Week End of Sea, Sailing and Cous Cous!

09/20/2023

Annette M.

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Switzerland

Abbiamo trascorso un bellissimo week-end sotto il sole (un pò meno il vento) della Sicilia, nel quale Davide ci ha viziati in tutti i modi: calette stupende dove fare il bagno, pasti più che squisiti e possibilità di approfitare del cous cous - Fest che si è svolto a San Vito lo Capo. Inoltre si è preoccupato ad organizzare tutto in maniera minuziosa e a farsi che ognuno si sia trovato a suo agio e benvenuto a bordo! Grazie capitano!

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