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Sicily holidays

Enjoy a Sicily (Italy) holiday aboard a boat

294 reviews

Experience a Sicily holiday where you can enjoy the best that Italy and the Mediterranean has to offer.

Choose from 61 experiences

670€

per spot

Christmas cruise from Catania to Malta

Port of departure: Catania, Italy

4 reviews

Next departure: 19 december

670€
450€

per spot

From Palermo via the Aeolian Islands to Catania

Port of departure: Palermo, PA, Italy

4 reviews

Next departure: 21 november

450€
450€

per spot

From Catania to Malta – sailing week to Valletta

Port of departure: Catania, Metropolitan city of Catania, Italy

4 reviews

Next departure: 28 november

450€
529€

per spot

The Navigator's Challenge — Crossing the Sicilian Coasts to Valencia

Port of departure: Palermo, Italy

2 reviews

Next departure: 22 mar 2027

529€
1,100€

per spot

The Egadi Islands aboard a brand new catamaran

Port of departure: Marsala, Trapani, Italie

3 reviews

Next departure: 28 aug 2027

1,100€
795€

per spot

Catamaran offshore sailing leg: Sicily - Sardinia

Port of departure: Catania, Italy

5 reviews

Next departure: 17 october

795€
650€

per spot

Sicily - "Aeolian Islands" on a catamaran

Port of departure: Capo d’Orlando, Messina, Italy

2 reviews

650€
850€

per spot

Sailing trip through Sicily: From Catania to the Aeolian Islands and Palermo

Port of departure: Catania, Italy

32 reviews

850€
1,340€

per spot

Large luxury catamaran with Hostess - Discovering the Aeolian Islands

Port of departure: Tonnarella, ME, Italy

1 review

1,340€
1,090€

per spot

Sailing holiday in Sicily, Aeolian Islands

Port of departure: Tonnarella, ME, Italy

2 reviews

1,090€
5,000€

Boat rental

Catamaran rental with skipper in the Egadi Islands

Port of departure: Marsala, Trapani, Italy

5,000€
10,450€

Boat rental

Sailing for a week on a catamaran to the Egadi islands

Port of departure: Palermo, Italy

10,450€

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Upcoming plans to sail in Sicily

Place	Start	Plazas		Price
,	From 17 Oct to 24 Oct 17 Oct 8 days	7	More information	Reserve for 795€ More information
Palermo,	From 21 Nov to 28 Nov 21 Nov 8 days	6	More information	Reserve for 450€ More information
Catania,	From 28 Nov to 5 Dec 28 Nov 8 days	6	More information	Reserve for 450€ More information
,	From 19 Dec to 27 Dec 19 Dec 9 days	6	More information	Reserve for 670€ More information
Palermo,	From 22 Mar to 31 Mar (2027) 22 Mar 10 days	7	More information	Reserve for 529€ More information
Capo d'Orlando,	From 12 Jun to 19 Jun (2027) 12 Jun 8 days	0	More information	No availability More information
Marsala,	From 28 Aug to 4 Sep (2027) 28 Aug 8 days	8	More information	Reserve for 1,100€ More information

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User reviews about Sicily holidays

5.00/5

Average grade

17

Valuations

Angela August of 2025

A week on a sailing boat in the Aeolian Islands

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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Samuel May of 2026

Dreamy Egadi Islands on a sailboat, setting sail from San Vito Lo Capo

Honestly, I would give this ten stars if I could… Jo & Andrea are not only seasoned sailors offering a unique way to enjoy the Egadi islands, they are also wonderful human beings who make you feel like family. For anyone looking for the BEST way to see NW Sicily, don’t hesitate! Grazie ragazzi!

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zaira August of 2025

A week on a sailing boat in the Aeolian Islands

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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Graciela May of 2026

Dreamy Egadi Islands on a sailboat, setting sail from San Vito Lo Capo

A very nice and recommended experience. Jo and Andrea were lovely, always attentive, close and aware that we were all well and enjoyed the trip.

The sailboat was very well kept and clean. In addition, I was traveling alone and I was very grateful for the family atmosphere they created. Thank you, Jo and Andrea

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Roberta September of 2026

Discovering the Aeolian Islands on a large, new Bali 5.4 catamaran

A wonderful experience, a wonderful boat, and a kind and attentive captain. I highly recommend it.

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Beatriz August of 2023

Sailing trip through Sicily: From Catania to the Aeolian Islands and Palermo

A great trip! Aroa and Carlos are charming and they treated us great. The journey was very beautiful, it definitely leaves you wanting more.
A highly recommended experience!

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