Sicily holidays | Sailing in Sicily

Choose from 41 experiences

From 600€

per spot

Let's discover the Aeolian Islands together by sailing

Port of departure: Furnari, ME, Italy

Next departure: 9 may 2026 · 24 dates available

From 600€
500€

per spot

Crossing from Palermo to Barcelona in an IMOCA

Port of departure: Palermo, Palerme, Italie

500€
Cancel free up to 15 days before

550€
495€

per spot

Navigation through the Egadi Islands

Port of departure: Balestrate, PA, Sicilia, Italy

Next departure: 3 apr 2026

550€ 495€
From 650€

per spot

Sicily - "Aeolian Islands" on a catamaran

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

1 review

Next departure: 28 mar 2026 · 6 dates available

From 650€
From 659€

per spot

Sicily - "Aeolian Islands"

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

1 review

Next departure: 28 mar 2026 · 13 dates available

From 659€
1,430€

per spot

Sailing and trekking among the Aeolian volcanoes, with an on-board mountain guide

Port of departure: Capo d'Orlando, ME, Italy

2 reviews

Next departure: 31 may 2026 · 1 dates available

1,430€
From 1,050€

per spot

The Egadi Islands aboard a brand new catamaran

Port of departure: Marsala, Trapani, Italie

3 reviews

Next departure: 9 may 2026 · 19 dates available

From 1,050€
1,100€

per spot

A week on a sailing boat in the Aeolian Islands

Port of departure: Lipari, ME, Italy

5 reviews

1,100€
1,340€

per spot

Discovering the Aeolian Islands on a Lagoon 42 catamaran

Port of departure: Capo d'Orlando, ME, Italy

1,340€
850€

per spot

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

Port of departure: Catania, Italy

32 reviews

850€
760€

per spot

Aeolian Islands on a sailing boat: nature, fun and lots of taste. Cook on board.

Port of departure: Marina di Portorosa, ME, Italy

2 reviews

760€
790€

per spot

Week in the blue painted blue of the Aeolian Islands

Port of departure: Lipari, Messine, Italie

7 reviews

790€

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Upcoming plans to sail in Sicily

Place	Start	Plazas		Price
Palermo, Italie	From 14 Nov to 17 Nov 14 Nov 4 days	6	More information	Reserve for 500€ More information
Capo d'Orlando,	From 28 Mar to 4 Apr (2026) 28 Mar 8 days	6	More information	Reserve for 659€ More information
Capo d'Orlando,	From 28 Mar to 4 Apr (2026) 28 Mar 8 days	6	More information	Reserve for 650€ More information
Alcamo,	From 3 Apr to 10 Apr (2026) 3 Apr 8 days	6	More information	Reserve for 495€ More information
Capo d'Orlando,	From 4 Apr to 11 Apr (2026) 4 Apr 8 days	6	More information	Reserve for 659€ More information
Capo d'Orlando,	From 4 Apr to 11 Apr (2026) 4 Apr 8 days	6	More information	Reserve for 650€ More information
Capo d'Orlando,	From 18 Apr to 25 Apr (2026) 18 Apr 8 days	6	More information	Reserve for 659€ More information
Capo d'Orlando,	From 18 Apr to 25 Apr (2026) 18 Apr 8 days	6	More information	Reserve for 650€ More information
Capo d'Orlando,	From 25 Apr to 2 May (2026) 25 Apr 8 days	6	More information	Reserve for 659€ More information
Capo d'Orlando,	From 25 Apr to 2 May (2026) 25 Apr 8 days	6	More information	Reserve for 650€ More information
Furnari,	From 9 May to 16 May (2026) 9 May 8 days	8	More information	Reserve for 600€ More information
Capo d'Orlando,	From 9 May to 16 May (2026) 9 May 8 days	6	More information	Reserve for 769€ More information
Capo d'Orlando,	From 9 May to 16 May (2026) 9 May 8 days	6	More information	Reserve for 849€ More information
Marsala,	From 9 May to 16 May (2026) 9 May 8 days	8	More information	Reserve for 1,050€ More information
Furnari,	From 16 May to 23 May (2026) 16 May 8 days	8	More information	Reserve for 600€ More information
Capo d'Orlando,	From 16 May to 23 May (2026) 16 May 8 days	6	More information	Reserve for 779€ More information
Capo d'Orlando,	From 16 May to 23 May (2026) 16 May 8 days	6	More information	Reserve for 869€ More information
Marsala,	From 16 May to 23 May (2026) 16 May 8 days	8	More information	Reserve for 1,050€ More information
Furnari,	From 23 May to 30 May (2026) 23 May 8 days	8	More information	Reserve for 600€ More information
Capo d'Orlando,	From 23 May to 30 May (2026) 23 May 8 days	6	More information	Reserve for 789€ More information
Capo d'Orlando,	From 23 May to 30 May (2026) 23 May 8 days	6	More information	Reserve for 889€ More information
Marsala,	From 23 May to 30 May (2026) 23 May 8 days	8	More information	Reserve for 1,100€ More information
Furnari,	From 30 May to 6 Jun (2026) 30 May 8 days	8	More information	Reserve for 600€ More information
Capo d'Orlando,	From 30 May to 6 Jun (2026) 30 May 8 days	6	More information	Reserve for 790€ More information
Marsala,	From 30 May to 6 Jun (2026) 30 May 8 days	8	More information	Reserve for 1,100€ More information
Capo d'Orlando,	From 31 May to 6 Jun (2026) 31 May 7 days	7	More information	Reserve for 1,430€ More information
Furnari,	From 6 Jun to 13 Jun (2026) 6 Jun 8 days	8	More information	Reserve for 600€ More information
Capo d'Orlando,	From 7 Jun to 13 Jun (2026) 7 Jun 7 days	7	More information	Reserve for 1,430€ More information
Furnari,	From 13 Jun to 20 Jun (2026) 13 Jun 8 days	8	More information	Reserve for 600€ More information
Marsala,	From 13 Jun to 20 Jun (2026) 13 Jun 8 days	8	More information	Reserve for 1,100€ More information
Furnari,	From 20 Jun to 27 Jun (2026) 20 Jun 8 days	8	More information	Reserve for 600€ More information
Marsala,	From 20 Jun to 27 Jun (2026) 20 Jun 8 days	8	More information	Reserve for 1,100€ More information
Furnari,	From 27 Jun to 4 Jul (2026) 27 Jun 8 days	8	More information	Reserve for 600€ More information
Marsala,	From 27 Jun to 4 Jul (2026) 27 Jun 8 days	8	More information	Reserve for 1,200€ More information
Furnari,	From 4 Jul to 11 Jul (2026) 4 Jul 8 days	5	More information	Reserve for 700€ More information
Marsala,	From 4 Jul to 11 Jul (2026) 4 Jul 8 days	8	More information	Reserve for 1,200€ More information
Furnari,	From 11 Jul to 18 Jul (2026) 11 Jul 8 days	8	More information	Reserve for 700€ More information
Marsala,	From 11 Jul to 18 Jul (2026) 11 Jul 8 days	8	More information	Reserve for 1,300€ More information
Furnari,	From 18 Jul to 25 Jul (2026) 18 Jul 8 days	8	More information	Reserve for 700€ More information
Marsala,	From 18 Jul to 25 Jul (2026) 18 Jul 8 days	8	More information	Reserve for 1,300€ More information
Furnari,	From 25 Jul to 1 Aug (2026) 25 Jul 8 days	8	More information	Reserve for 700€ More information
Marsala,	From 25 Jul to 1 Aug (2026) 25 Jul 8 days	10800	More information	Reserve for 1,400€ More information
Furnari,	From 1 Aug to 8 Aug (2026) 1 Aug 8 days	8	More information	Reserve for 800€ More information
Marsala,	From 1 Aug to 8 Aug (2026) 1 Aug 8 days	8	More information	Reserve for 1,400€ More information
Furnari,	From 8 Aug to 15 Aug (2026) 8 Aug 8 days	8	More information	Reserve for 800€ More information
Marsala,	From 8 Aug to 15 Aug (2026) 8 Aug 8 days	6	More information	Reserve for 1,500€ More information
Furnari,	From 15 Aug to 22 Aug (2026) 15 Aug 8 days	8	More information	Reserve for 800€ More information
Marsala,	From 15 Aug to 22 Aug (2026) 15 Aug 8 days	8	More information	Reserve for 1,500€ More information
Furnari,	From 22 Aug to 29 Aug (2026) 22 Aug 8 days	8	More information	Reserve for 800€ More information
Marsala,	From 22 Aug to 29 Aug (2026) 22 Aug 8 days	8	More information	Reserve for 1,300€ More information
Furnari,	From 29 Aug to 5 Sep (2026) 29 Aug 8 days	8	More information	Reserve for 700€ More information
Marsala,	From 29 Aug to 5 Sep (2026) 29 Aug 8 days	8	More information	Reserve for 1,200€ More information
Furnari,	From 5 Sep to 12 Sep (2026) 5 Sep 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 5 Sep to 12 Sep (2026) 5 Sep 8 days	6	More information	Reserve for 790€ More information
Marsala,	From 5 Sep to 12 Sep (2026) 5 Sep 8 days	8	More information	Reserve for 1,200€ More information
Furnari,	From 12 Sep to 19 Sep (2026) 12 Sep 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 12 Sep to 19 Sep (2026) 12 Sep 8 days	6	More information	Reserve for 775€ More information
Marsala,	From 12 Sep to 19 Sep (2026) 12 Sep 8 days	8	More information	Reserve for 1,100€ More information
Furnari,	From 19 Sep to 26 Sep (2026) 19 Sep 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 19 Sep to 26 Sep (2026) 19 Sep 8 days	6	More information	Reserve for 750€ More information
Marsala,	From 19 Sep to 26 Sep (2026) 19 Sep 8 days	8	More information	Reserve for 1,100€ More information
Furnari,	From 26 Sep to 3 Oct (2026) 26 Sep 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 26 Sep to 3 Oct (2026) 26 Sep 8 days	6	More information	Reserve for 699€ More information
Marsala,	From 26 Sep to 3 Oct (2026) 26 Sep 8 days	8	More information	Reserve for 1,050€ More information
Furnari,	From 3 Oct to 10 Oct (2026) 3 Oct 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 3 Oct to 10 Oct (2026) 3 Oct 8 days	6	More information	Reserve for 699€ More information
Furnari,	From 10 Oct to 17 Oct (2026) 10 Oct 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 10 Oct to 17 Oct (2026) 10 Oct 8 days	6	More information	Reserve for 699€ More information
Furnari,	From 17 Oct to 24 Oct (2026) 17 Oct 8 days	8	More information	Reserve for 700€ More information
Furnari,	From 24 Oct to 31 Oct (2026) 24 Oct 8 days	8	More information	Reserve for 700€ More information

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User reviews about Sicily holidays

5.00/5

Average grade

Valuations

simona July of 2025

The Egadi Islands aboard a brand new catamaran

Peppe, a super captain with a kind heart and manner. Fantastic crew. Fantastic experience.
We'll see each other again soon.

Eleni June of 2025

Aeolian Islands by sailboat: the charm of the blue sea

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!

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!

Rosa K. September of 2024

Aeolian Islands on a sailing boat: nature, fun and lots of taste. Cook on board.

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.!!!

Bet August of 2023

Aeolian Islands on a sailing boat: nature, fun and lots of taste. Cook on board.

They have been wonderful days despite the bad weather, we have felt safe with Giacomo at all times. Giacomo and Laura are charming hosts, Laura's cuisine is spectacular, the surroundings are unbeatable and the navigation, despite being short due to the weather, is very pleasant. We recommend it for sure!

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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