
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.
12
experiences

5.0
Super!
Italy: Sicily
1 day - 0 nights
One departure available
June
€98
Per person

4.7
Italy: Sicily
4 days - 3 nights
2 departures available
September
Starting from
€345
€311
Per person

5.0
Italy: Sicily
5 days - 5 nights
One departure available
July
€1,000
Per person

4.4
Italy: Sicily
6 days - 7 nights
One departure available
June - July
€935
Per person

Italy: Sicily
2 days - 1 night
14 departures available
June - September
Starting from
€215
€194
Per person

4.6
Italy: Sicily
4 days - 3 nights
2 departures available
September
€350
€315
Per person

4.4
Italy: Sicily
6 days - 7 nights
One departure available
August
€660
Per person

5.0
Italy: Sicily
4 days - 3 nights
2 departures available
September
€345
Per person

5.0
Italy: Sicily
5 days - 4 nights
One departure available
September
€380
Per person

4.4
Italy: Sicily
6 days - 7 nights
One departure available
June
€789
€671
Per person

Italy: Sicily
3 days - 2 nights
14 departures available
June - September
Starting from
€315
€284
Per person

4.9
Italy: Sicily
3 days - 3 nights
4 departures available
July - August
Starting from
€360
Per person
Why book a holiday with Sailsquare?
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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
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 more about the skipper and travellers who have already booked the holiday, to find out more about the
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
37 reviews
COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!
09/30/2025
Francesco P.
-
IT
COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!
09/24/2025
Nicola V.
-
IT
Ten days from Catania to the Aeolian Islands on a luxury sailboat
08/27/2025
Marta B.
-
IT
Ten days from Catania to the Aeolian Islands on a luxury sailboat
08/26/2025
Mario L.
-
IT
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