Sicily holidays | Sailing in Sicily

Choose from 11 experiences

890€

per spot

Sailing holiday in Sicily, Aeolian Islands

Port of departure: Tonnarella, ME, Italy

Next departure: 5 september · 3 dates available

890€
From 980€

per spot

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

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

Next departure: 19 september · 3 dates available

From 980€
From 690€

per spot

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

Port of departure: Porto Pignataro, Lipari

2 reviews

Next departure: 5 september · 2 dates available

From 690€
690€

per spot

Week in the blue painted blue of the Aeolian Islands

Port of departure: Portorosa, Sicilia

6 reviews

Next departure: 5 september

690€
From 700€

per spot

Let's discover the Aeolian Islands together by sailing

Port of departure: Furnari, ME, Italy

2 reviews

Next departure: 12 september · 6 dates available

From 700€
From 890€

per spot

Sailing for a week in the Aeolian Islands

Port of departure: Lipari, ME, Italy

8 reviews

Next departure: 5 september

From 890€
Cancel free up to 15 days before

650€
585€

per spot

Navigation through the Egadi Islands

Port of departure: Balestrate, PA, Sicilia, Italy

Next departure: 6 september

650€ 585€
From 699€

per spot

Sicily - "Aeolian Islands"

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

2 reviews

Next departure: 5 september · 5 dates available

From 699€
From 950€

per spot

The Egadi Islands aboard a brand new catamaran

Port of departure: Marsala, Trapani, Italie

3 reviews

Next departure: 26 september · 1 dates available

From 950€
From 650€

per spot

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

Port of departure: San Vito Lo Capo, TP, Italy

5 reviews

Next departure: 12 september · 2 dates available

From 650€
795€

per spot

Catamaran offshore sailing leg: Sicily - Sardinia

Port of departure: Catania, Italy

4 reviews

Next departure: 17 october

795€

Upcoming plans to sail in Sicily

Place	Start	Plazas		Price
Furnari,	From 5 Sep to 12 Sep 5 Sep 8 days	0	More information	No availability More information
Capo d'Orlando,	From 5 Sep to 12 Sep 5 Sep 8 days	1	More information	Reserve for 790€ More information
Lipari,	From 5 Sep to 12 Sep 5 Sep 8 days	6	More information	Reserve for 890€ More information
Lipari,	From 5 Sep to 12 Sep 5 Sep 8 days	4	More information	Reserve for 990€ More information
,	From 5 Sep to 12 Sep 5 Sep 8 days	0	More information	No availability More information
Lipari,	From 5 Sep to 12 Sep 5 Sep 8 days	8	More information	Reserve for 690€ More information
Tonnarella,	From 5 Sep to 12 Sep 5 Sep 8 days	8	More information	Reserve for 890€ More information
Alcamo,	From 6 Sep to 13 Sep 6 Sep 8 days	3	More information	Reserve for 585€ More information
Furnari,	From 12 Sep to 19 Sep 12 Sep 8 days	6	More information	Reserve for 700€ More information
Capo d'Orlando,	From 12 Sep to 19 Sep 12 Sep 8 days	4	More information	Reserve for 775€ More information
Lipari,	From 12 Sep to 19 Sep 12 Sep 8 days	6	More information	Reserve for 790€ More information
Lipari,	From 12 Sep to 19 Sep 12 Sep 8 days	0	More information	No availability More information
,	From 12 Sep to 19 Sep 12 Sep 8 days	8	More information	Reserve for 750€ More information
Tonnarella,	From 12 Sep to 19 Sep 12 Sep 8 days	0	More information	No availability More information
Tonnarella,	From 12 Sep to 19 Sep 12 Sep 8 days	2	More information	Reserve for 1,050€ More information
Furnari,	From 19 Sep to 26 Sep 19 Sep 8 days	6	More information	Reserve for 700€ More information
Capo d'Orlando,	From 19 Sep to 26 Sep 19 Sep 8 days	4	More information	Reserve for 750€ More information
Marsala,	From 19 Sep to 26 Sep 19 Sep 8 days	0	More information	No availability More information
Lipari,	From 19 Sep to 26 Sep 19 Sep 8 days	6	More information	Reserve for 690€ More information
Tonnarella,	From 19 Sep to 26 Sep 19 Sep 8 days	2	More information	Reserve for 890€ More information
Capo d'Orlando,	From 19 Sep to 26 Sep 19 Sep 8 days	10	More information	Reserve for 980€ More information
Furnari,	From 26 Sep to 3 Oct 26 Sep 8 days	5	More information	Reserve for 700€ More information
Capo d'Orlando,	From 26 Sep to 3 Oct 26 Sep 8 days	6	More information	Reserve for 699€ More information
Marsala,	From 26 Sep to 3 Oct 26 Sep 8 days	8	More information	Reserve for 950€ More information
Capo d'Orlando,	From 26 Sep to 3 Oct 26 Sep 8 days	10	More information	Reserve for 980€ More information
Furnari,	From 3 Oct to 10 Oct 3 Oct 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 3 Oct to 10 Oct 3 Oct 8 days	4	More information	Reserve for 699€ More information
,	From 3 Oct to 10 Oct 3 Oct 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 3 Oct to 10 Oct 3 Oct 8 days	10	More information	Reserve for 980€ More information
Furnari,	From 10 Oct to 17 Oct 10 Oct 8 days	8	More information	Reserve for 700€ More information
Capo d'Orlando,	From 10 Oct to 17 Oct 10 Oct 8 days	4	More information	Reserve for 699€ More information
,	From 10 Oct to 17 Oct 10 Oct 8 days	8	More information	Reserve for 650€ More information
Capo d'Orlando,	From 10 Oct to 17 Oct 10 Oct 8 days	10	More information	Reserve for 980€ More information
Furnari,	From 17 Oct to 24 Oct 17 Oct 8 days	8	More information	Reserve for 700€ More information
,	From 17 Oct to 24 Oct 17 Oct 8 days	7	More information	Reserve for 795€ More information
Furnari,	From 24 Oct to 31 Oct 24 Oct 8 days	8	More information	Reserve for 700€ More information
Marsala,	From 28 Aug to 4 Sep (2027) 28 Aug 8 days	8	More information	Reserve for 1,100€ More information

Show all dates

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User reviews about Sicily holidays

5.00/5

Average grade

Valuations

CRISTINA May of 2026

Let's discover the Aeolian Islands together by sailing

Beautiful cruise.
The wind, stronger than one would have wished for a sailing trip, and the weather, which did not spare a few drops of rain, were handled by the "commander" with realistic prudence, without ever dramatizing things beyond what was necessary, transforming contingencies into opportunities.
We will return

Pilar June of 2026

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

It has been wonderful, the ship and its commanders, their kindness, availability and adaptation to the group
The
beautiful islands, the incredible sea, the great group and I'll be back for sure to experience that beauty. Totally recommended

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.!!!

Roberta August of 2026

Let's discover the Aeolian Islands together by sailing

A wonderful experience! Mario was exceptional: helpful, friendly, and always attentive to our needs. A skilled skipper and expert navigator, he showed us wonderful and lesser-known places and gave us valuable tips for our vacation. An unforgettable experience full of laughs!

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!

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!

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