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Sicily holidays

Enjoy a Sicily (Italy) holiday aboard a boat
97 reviews
Experience a Sicily holiday where you can enjoy the best that Italy and the Mediterranean has to offer.
Choose from 44 experiences
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Upcoming plans to sail in Sicily
Place Start Plazas Price
Tonnarella,
From 18 Oct to 25 Oct
18 Oct
8 days
6 More information Reserve for 680€
Tonnarella,
From 25 Oct to 1 Nov
25 Oct
8 days
6 More information Reserve for 680€
Furnari,
From 9 May to 16 May (2026)
9 May
8 days
8 More information Reserve for 600€
Furnari,
From 16 May to 23 May (2026)
16 May
8 days
8 More information Reserve for 600€
Furnari,
From 23 May to 30 May (2026)
23 May
8 days
8 More information Reserve for 600€
Furnari,
From 30 May to 6 Jun (2026)
30 May
8 days
8 More information Reserve for 600€
Capo d'Orlando,
From 31 May to 6 Jun (2026)
31 May
7 days
7 More information Reserve for 1,430€
Furnari,
From 6 Jun to 13 Jun (2026)
6 Jun
8 days
8 More information Reserve for 600€
Capo d'Orlando,
From 7 Jun to 13 Jun (2026)
7 Jun
7 days
7 More information Reserve for 1,430€
Furnari,
From 13 Jun to 20 Jun (2026)
13 Jun
8 days
8 More information Reserve for 600€
Furnari,
From 20 Jun to 27 Jun (2026)
20 Jun
8 days
8 More information Reserve for 600€
Furnari,
From 27 Jun to 4 Jul (2026)
27 Jun
8 days
8 More information Reserve for 600€
Furnari,
From 4 Jul to 11 Jul (2026)
4 Jul
8 days
5 More information Reserve for 700€
Furnari,
From 11 Jul to 18 Jul (2026)
11 Jul
8 days
8 More information Reserve for 700€
Furnari,
From 18 Jul to 25 Jul (2026)
18 Jul
8 days
8 More information Reserve for 700€
Furnari,
From 25 Jul to 1 Aug (2026)
25 Jul
8 days
8 More information Reserve for 700€
Furnari,
From 1 Aug to 8 Aug (2026)
1 Aug
8 days
8 More information Reserve for 800€
Furnari,
From 8 Aug to 15 Aug (2026)
8 Aug
8 days
8 More information Reserve for 800€
Furnari,
From 15 Aug to 22 Aug (2026)
15 Aug
8 days
8 More information Reserve for 800€
Furnari,
From 22 Aug to 29 Aug (2026)
22 Aug
8 days
8 More information Reserve for 800€
Furnari,
From 29 Aug to 5 Sep (2026)
29 Aug
8 days
8 More information Reserve for 700€
Furnari,
From 5 Sep to 12 Sep (2026)
5 Sep
8 days
8 More information Reserve for 700€
Furnari,
From 12 Sep to 19 Sep (2026)
12 Sep
8 days
8 More information Reserve for 700€
Furnari,
From 19 Sep to 26 Sep (2026)
19 Sep
8 days
8 More information Reserve for 700€
Furnari,
From 26 Sep to 3 Oct (2026)
26 Sep
8 days
8 More information Reserve for 700€
Furnari,
From 3 Oct to 10 Oct (2026)
3 Oct
8 days
8 More information Reserve for 700€
Furnari,
From 10 Oct to 17 Oct (2026)
10 Oct
8 days
8 More information Reserve for 700€
Furnari,
From 17 Oct to 24 Oct (2026)
17 Oct
8 days
8 More information Reserve for 700€
Furnari,
From 24 Oct to 31 Oct (2026)
24 Oct
8 days
8 More information Reserve for 700€
Show all dates
User reviews about Sicily holidays
5.00/5
Average grade
8
Valuations
A wonderful experience.
Thank you Leonardo for showing us the beautiful and amazing spots of the Eolian Islands' volcanic scenery.
We loved the sailing part, even in the rough weather.
We always felt safe and comfortable.
And thank you Luigi for the gastronomie!
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As Good as It Gets - It doesn't get any better than this! A wonderful trip with Giacomo, who is not only a very pleasant, humorous, fun-loving and experienced skipper, but also accompanied us on great island trips....
His well-organized tour is highly recommended all around.!!!
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A fantastic experience with Giampiero and Raffaella!!! It wasn't my first sailing holiday, but I felt truly pampered every step of the way with them. Giampiero is a professional, kind, and attentive skipper! The boat was impeccable, and Raffaella provided top-notch service. Complete relaxation, an experience I'll repeat!
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Peppe, a super captain with a kind heart and manner. Fantastic crew. Fantastic experience.
We'll see each other again soon.
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My first sailing holiday, and Giampiero and Raffaella were fantastic. They made me feel safe and comfortable, always choosing the best spots to make me feel at ease. Kind, attentive, and welcoming. A special experience!
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It was a pleasure of getting to know the beautiful Italian Islands and especially enjoying the wonderful ambience onboard.
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