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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.

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Sailing from Trapani to San Vito Lo Capo

Italy: Sicily

5 days - 4 nights

One departure available

September

€380

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

6 departures available

August - September

Starting from

€215

€194

Per person

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4.6

Cous Cous Fest: weekend of Sailing, Music and Cous Cous!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€350

€315

Per person

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4.9

Calabria and Sicily by luxury boat

Italy: Sicily

6 days - 7 nights

One departure available

August

€850

€700

Per person

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4.4

Calabria and Sicily sailing: from Crotone to Catania with a view of Mount Etna

Italy: Sicily

6 days - 7 nights

One departure available

August

€660

Per person

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4.8

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

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

€311

Per person

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5.0

Sailing day in the beautiful Marine Protected Area of Capo Milazzo

Italy: Sicily

1 day - 0 nights

2 departures available

August

€118

Per person

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Mid-August among the big islands: from Sardinia to Sicily

Italy: Sicily

6 days - 7 nights

One departure available

August

€900

Per person

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5.0

3 days sailing among the hidden gems of Palermo - All inclusive & flexible dates

Italy: Sicily

3 days - 2 nights

6 departures available

August - September

Starting from

€315

€284

Per person

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4.9

Families seafaring! Three days on a boat for young and old.

Italy: Sicily

3 days - 3 nights

2 departures available

August

Starting from

€480

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Sicily

38 reviews

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2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

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IT

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

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

09/30/2025

Francesco P.

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IT

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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IT

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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IT

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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