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Sailing and catamaran holidays and cruises in Sicily

Exploring the Sicilian coastline by sailboat is a journey between the magic of San Vito lo Capo and the wild beauty of the Zingaro Reserve. The turquoise waters of the Tyrrhenian Sea frame majestic cliffs and secret bays, offering a sailing experience wrapped in an unparalleled natural setting. Every moment is an opportunity to discover the true essence of Sicily, a blend of ancient charm and unspoilt landscapes that leave an indelible imprint on the hearts of those who sail there.

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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 - Sailing and catamaran holidays and cruises in Sicily

45 reviews

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COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

09/30/2025

Francesco P.

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Italy

We spent three wonderful days on a boat in San Vito Lo Capo together with Giovanni, an exceptional skipper and a truly amazing cook! 🌊⛵️ From the first moment we felt welcomed and pampered: Giovanni was able to combine professionalism, sympathy and passion for the sea, creating a relaxed and cheerful atmosphere. Each day was a small journey through pristine coves, dives into crystal clear waters and unforgettable sunsets. But the real surprise was his dishes: authentic flavors, cooked with love and taste, which made the experience even more special. It was a vacation that rejuvenated our body and mind — fun, relaxing, and full of excitement. We really recommend it to everyone: let yourself be guided by the wind, the sea and Giovanni's hospitality... you won't regret it! 💙✨
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COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

09/24/2025

Nicola V.

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Italy

A holiday that respected the plans in the best way, kissed by a favorable climate and created a condition where positivity prevailed.... Daniele, nice and professional, was an integral part of the context despite his role played in a decent way... Place and context already known in the past.... Returning and being hosted by a new skipper did not make me think too much considering that it was part of a context of guaranteed colleagues. His availability was repaid with equal gratitude. The same was accompanied by a nice group with whom to share special moments.
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Ten days from Catania to the Aeolian Islands on a luxury sailboat

08/27/2025

Marta B.

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Italy

It was my first sailing holiday and I will always carry these 10 days in my heart! :) The skippers Paco and Gabriella were very helpful, kind and attentive, able to convey their passion for the sea and create that special atmosphere that makes you feel immediately at home. The boat was very beautiful and with all the comforts for a relaxing holiday. The navigation was wonderful, with the wind and the sea giving a feeling of absolute freedom, the spectacular sunsets seen from the boat and even the unique experience of crossing the Strait of Messina under sail! The trip was made even more enjoyable by the delicious food and sharing moments on board, as well as the company of wonderful people I met. A holiday that made me fall in love with life on a boat and that I recommend to anyone who wants to discover the Aeolian Islands, Sicily and even a piece of Calabria from an authentic and magical perspective.
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Ten days from Catania to the Aeolian Islands on a luxury sailboat

08/26/2025

Mario L.

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Italy

FABULOUS holiday, and to say it a demanding Milanese..... the two "captains" Gabriella and Paco are delightful people, prepared, kind, attentive and truly dedicated to the well-being and happiness of the crew. We also did some sailing school and "introduction" to life as a boat, always maintaining the highest standards of marine safety. The destinations we reached were of greatest interest to me: Tropea, Panarea, the Archaeological Museum of RC (with the Bronzes...), the ascent to the volcano of Vulcano and others. They always tried to make us try bays, inlets and always varied experiences, without sparing themselves in the slightest! We sailed as often as we could! Gabriella also not only knows how to prepare excellent dishes but encourages the crew to propose and prepare new ones. Really nice people with whom to have a nice chat. We had a really great time also helped by luck, the crew was fantastic! I RECOMMEND [hidden] Sailing ABSOLUTELY! PS boat TOP!!

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