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Sailboat yacht sailing holidays & tours in Sicily

Discover more than 12 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!

Sailing day in the beautiful Marine Protected Area of Capo Milazzo

Italy: Sicily

1 day - 0 nights

One departure available

June

€98

Per person

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4.4

Week from the Egadi Islands to the Aeolian Islands with hostess

Italy: Sicily

6 days - 7 nights

One departure available

June - July

€935

Per person

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New

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

Italy: Sicily

2 days - 1 night

19 departures available

May - 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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4.7

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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4.7

Offshore School from Lampedusa to Sicily

Italy: Sicily

7 days - 7 nights

One departure available

May - June

€650

Per person

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5.0

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

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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4.4

From Termini Imerese to the Egadi Islands with skipper and hostess

Italy: Sicily

6 days - 7 nights

One departure available

June

€739

Per person

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New

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

Italy: Sicily

3 days - 2 nights

16 departures available

May - September

Starting from

€315

€284

Per person

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4.1

East Coast of Sicily From Taormina to Portopalo. Cook on board

Italy: Sicily

6 days - 7 nights

4 departures available

April - May

€650

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

4 departures available

July - August

Starting from

€360

€324

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Sicily

37 reviews

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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