Sicily holidays | Sailing in Sicily

Choose from 44 experiences

680€

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

Next departure: 27 september · 4 dates available

680€
540€
513€

per spot

Week in the blue painted blue of the Aeolian Islands

Port of departure: Lipari, Messine, Italie

7 reviews

Next departure: 20 september

540€ 513€
1,340€

per spot

Large luxury catamaran with Hostess - Discovering the Aeolian Islands

Port of departure: Tonnarella, ME, Italy

Next departure: 20 september

1,340€
599€

per spot

Sicily - "Aeolian Islands"

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

1 review

Next departure: 27 september · 2 dates available

599€
699€

per spot

Mileage trip approx. 400 NM from Siracusa to Carloforte

Port of departure: Siracusa, Syrakus, Italy

3 reviews

Next departure: 12 october

699€
1,000€

per spot

The Egadi Islands aboard a brand new catamaran

Port of departure: Marsala, Trapani, Italie

1 review

Next departure: 27 september

1,000€
1,100€

per spot

A week on a sailing boat in the Aeolian Islands

Port of departure: Lipari, ME, Italy

2 reviews

1,100€
850€

per spot

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

Port of departure: Catania, Italy

32 reviews

850€
475€

per spot

Nautical cruise through Sicily and to the south of Sardinia

Port of departure: Trapani, Italy

32 reviews

475€
790€

per spot

Week in the blue painted blue of the Aeolian Islands

Port of departure:

6 reviews

790€
700€

per spot

Discovering the Aeolian Islands

Port of departure: Milazzo, ME, Italy

700€
6,100€

Boat rental

Weekly cruise to the Aeolian islands on a sailing boat

Port of departure: Palermo, Italy

6,100€

Show more experiences

Upcoming plans to sail in Sicily

Place	Start	Plazas		Price
Tonnarella,	From 20 Sep to 27 Sep 20 Sep 8 days	0	More information	No availability More information
Lipari,	From 20 Sep to 26 Sep 20 Sep 7 days	8	More information	Reserve for 513€ More information
Capo d'Orlando,	From 20 Sep to 27 Sep 20 Sep 8 days	0	More information	No availability More information
Tonnarella,	From 20 Sep to 27 Sep 20 Sep 8 days	8	More information	Reserve for 1,340€ More information
Marsala,	From 27 Sep to 4 Oct 27 Sep 8 days	3	More information	Reserve for 1,000€ More information
Capo d'Orlando,	From 27 Sep to 4 Oct 27 Sep 8 days	1	More information	Reserve for 599€ More information
Capo d'Orlando,	From 27 Sep to 4 Oct 27 Sep 8 days	0	More information	No availability More information
Tonnarella,	From 27 Sep to 4 Oct 27 Sep 8 days	0	More information	No availability More information
Tonnarella,	From 27 Sep to 4 Oct 27 Sep 8 days	6	More information	Reserve for 680€ More information
Capo d'Orlando,	From 4 Oct to 11 Oct 4 Oct 8 days	6	More information	Reserve for 599€ More information
Capo d'Orlando,	From 4 Oct to 11 Oct 4 Oct 8 days	0	More information	No availability More information
Tonnarella,	From 4 Oct to 11 Oct 4 Oct 8 days	6	More information	Reserve for 680€ More information
Poros,	From 5 Oct to 20 Oct 5 Oct 16 days	0	More information	No availability More information
Capo d'Orlando,	From 11 Oct to 18 Oct 11 Oct 8 days	4	More information	Reserve for 599€ More information
Capo d'Orlando,	From 11 Oct to 18 Oct 11 Oct 8 days	0	More information	No availability More information
Tonnarella,	From 11 Oct to 18 Oct 11 Oct 8 days	6	More information	Reserve for 680€ More information
Siracusa,	From 12 Oct to 19 Oct 12 Oct 8 days	6	More information	Reserve for 699€ More information
Tonnarella,	From 18 Oct to 25 Oct 18 Oct 8 days	6	More information	Reserve for 680€ More information
Tonnarella,	From 25 Oct to 1 Nov 25 Oct 8 days	6	More information	Reserve for 680€ More information

Show all dates

User reviews about Sicily holidays

5.00/5

Average grade

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!

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.!!!

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!

Niels July of 2025

Week in the blue painted blue of the Aeolian Islands

It was a pleasure of getting to know the beautiful Italian Islands and especially enjoying the wonderful ambience onboard.

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!

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!

See more opinions