Sicily holidays | Sailing in Sicily

Choose from 45 experiences

From 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: 6 september

From 680€
From
540€
513€

per spot

Week in the blue painted blue of the Aeolian Islands

Port of departure: Lipari, Messine, Italie

7 reviews

Next departure: 30 august · 2 dates available

From 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€
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: 6 september · 1 dates available

550€ 495€
1,120€
1,064€

per spot

We travel the world: Mile-long cruise from the Aegean to Sicily with Vulkan

Port of departure: Poros, Greece

2 reviews

Next departure: 5 october

1,120€ 1,064€
890€

per spot

Sailing for a week in the Aeolian Islands

Port of departure: Lipari, ME, Italy

8 reviews

Next departure: 30 august

890€
599€

per spot

Sicily - "Aeolian Islands"

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

1 review

Next departure: 27 september · 2 dates available

599€
From 1,200€

per spot

Catamaran Holiday in the Egadi with Hostess/Cook – Luxury and Relaxation at Sea

Port of departure: Marsala, Trapani, Italie

1 review

Next departure: 6 september · 1 dates available

From 1,200€
From 849€

per spot

Sicily - "Aeolian Islands" on a catamaran

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

1 review

Next departure: 6 september

From 849€
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€
From 1,000€

per spot

The Egadi Islands aboard a brand new catamaran

Port of departure: Marsala, Trapani, Italie

1 review

Next departure: 6 september · 2 dates available

From 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€

Show more experiences

Upcoming plans to sail in Sicily

Place	Start	Plazas		Price
Tonnarella,	From 30 Aug to 6 Sep 30 Aug 8 days	0	More information	No availability More information
Lipari,	From 30 Aug to 6 Sep 30 Aug 8 days	6	More information	Reserve for 890€ More information
Marsala,	From 30 Aug to 6 Sep 30 Aug 8 days	0	More information	No availability More information
Lipari,	From 30 Aug to 5 Sep 30 Aug 7 days	8	More information	Reserve for 655€ More information
Marsala,	From 30 Aug to 6 Sep 30 Aug 8 days	0	More information	No availability More information
Tonnarella,	From 6 Sep to 13 Sep 6 Sep 8 days	2	More information	Reserve for 880€ More information
Marsala,	From 6 Sep to 13 Sep 6 Sep 8 days	8	More information	Reserve for 1,200€ More information
Lipari,	From 6 Sep to 12 Sep 6 Sep 7 days	8	More information	Reserve for 560€ More information
Capo d'Orlando,	From 6 Sep to 13 Sep 6 Sep 8 days	2	More information	Reserve for 990€ More information
Marsala,	From 6 Sep to 13 Sep 6 Sep 8 days	8	More information	Reserve for 1,300€ More information
Alcamo,	From 6 Sep to 13 Sep 6 Sep 8 days	6	More information	Reserve for 495€ More information
Tonnarella,	From 13 Sep to 20 Sep 13 Sep 8 days	0	More information	No availability More information
Marsala,	From 13 Sep to 20 Sep 13 Sep 8 days	4	More information	Reserve for 1,100€ More information
Capo d'Orlando,	From 13 Sep to 20 Sep 13 Sep 8 days	0	More information	No availability More information
Marsala,	From 13 Sep to 20 Sep 13 Sep 8 days	8	More information	Reserve for 1,200€ More information
Alcamo,	From 13 Sep to 20 Sep 13 Sep 8 days	6	More information	Reserve for 495€ More information
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	6	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
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
Poros,	From 5 Oct to 20 Oct 5 Oct 16 days	7	More information	Reserve for 1,064€ 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
Siracusa,	From 12 Oct to 19 Oct 12 Oct 8 days	6	More information	Reserve for 699€ More information

Show all dates

User reviews about Sicily holidays

5.00/5

Average grade

Valuations

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!

Pilar Beatriz July of 2025

Discover Sicily and the Aeolian Islands sailing on our sailing school boat

Great professionalism. I would repeat without hesitation.

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!

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!

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.!!!

See more opinions