Sailing Itinerary – 2 weeks in Sicily

Praised by songs and poems, Sicily needs no real introduction. Located at the southern tip of Italy, it is the biggest island in the Mediterranean. It’s only 32 km distant from the mainland of Italy, but still encloses every beauty of a wild Island. Whenever you are interested in turquoise bays, snorkeling or diving spots, historical ruins, or tasty food, Sicily can make all your wishes come true. 

Here we have summarised all our knowledge about Sicily and laid out the perfect sailing Itinerary for two weeks along the coast of Sicily. If you have only one week at hand, we would recommend you to skip the Aeolian Islands, or primarily visit the Aeolian Islands. At the end of the blogpost, we display different ideal sailing routes for one week, depending on your starting point. Moreover, we will make a specific blog post about the perfect Sailing route in the Aeolian Islands.

1 – Palermo

Palermo, the starting point of our Sicilian sailing itinerary, is a city of opposites. Beautiful historical buildings opposed to trashy neighborhoods, famous anti-mafia fighters opposed to the head of most mafia families, delightful meals opposed to, well nothing really food is excellent everywhere in Palermo :). The marinas of the city do not really stand out for luxury. Still, thery are not very expensive and are a good starting point to visit the city.

2 – Cefalu

Tourists pretty much overrun this small Italian town, and most of its small streets are filled with tourist shops and restaurants. But luckily, they moved the marina behind the hill, allowing sailors to enjoy the beauty of the surrounding landscape without the masses of tourists. Moreover, you don’t even have to venture inside of the town to get one of the best pizzas we had so far (and trust us, we tasted a whole lot of pizzas in our life 🙂 ). Head up to the lighthouse to find three restaurants overseeing the sea and sit down at “Da Sasá” for a pizza and the most spectacular sunset. You can obviously head further to visit the town which has reasons to be overrun by tourists, but we believe you will find your way back to the quietness and crystal clear water of the marina.

3 – Lipari

Lipari, the main islands of the Aeolian Islands, is easily reachable in an afternoon sail from Milazzo, Sicily. Once there, you can choose between anchoring in front of the castle, three floating docks without showers close to the town, or a bigger floating dock more north with showers, but about 2km distant from the town. The prices do not seem to vary between the docks, but you should always call them and ask for prices as there might be changes. Lipari itself is a beautiful town, overseen by a magnificent medieval Castel which can be visited during the day. Moreover, Lipari is an excellent starting point o visit all the Aeolian Islands. We would recommend a day trip to Panarea and Spinazzola, the less-visited Islands, which feature beautiful bays with cliffs and crystal clear waters. For more tips about the Aeolian Islands, read on here.

4 – Stromboli

The most famous of the Aeolian Islands, since it hosts the most active volcano in the world, should not be missed during your two-week sail in Sicily. Unfortunately, there is no protected bay to anchor safely around Stromboli, so you will have to choose the right weather window to visit it. But we warmly recommend the extra planning to be able to admire the red sparks of the volcano while sipping your favorite drink on the boat. On our way from Lipari to Stromboli we caught our first tuna, so don’t forget to throw in your fishing line while sailing (if the seasonal restrictions do allow it).

Entrance to the strait of messina on a sailboat

 5 – The Strait of Messina

The Strait of Messina is a real treasure of sailing experience. Feard by navigators for thousands of years, it still is a thrill to navigate through its whirlpools and tides, even if today we know they don’t originate from mystical seamonsters. We wrote a very extensive blog post about the Strait of Messina. Make sure you read that before sailing through it as the Strait still poses many challenges for all sailors.

6 – Taormina

Famous for its greek theater, this small Italian town has every reason to be acclaimed as it is. Unfortunately, it is one of those beauties which are not visible from a sailboat, so you will have to get on land and head up to the town. There are good anchoring possibilities in front of the town and also buoys for those who prefer. Take the bus up to the town and get lost in the small streets after viewing the sea from the greek theater. Trust us this expereince will give you a whole new perspective on our much-loved sea.

7 – Catania

Catania, the end of our sailing itinerary, and probably the worst marina you will ever visit. The only positive part of the marina is the location at the heart of the city, which will allow you to discover the city easily. If you go there, don’t miss the chance to eat at one of the best restaurants ever, the “Gambero pazzo”. Make sure to have a reservation as its cuisine is well known, and you rarely find a spot. 

sailing itinerary one week in sicily

If you only have one week at your disposal, we have ideated sailing trips from Palermo and Catania. These sailing itineraries assume that you charter a boat and therefore have to return it at the starting point.

sailing itinerary one week in sicily

We hope you found this blog post useful and inspiring. If you have more questions regarding sailing in Sicily, please let us know in the comments, and we will try to answer as quickly as possible. If you are not sure yet if Sicily is the right place for your next sailing trip, click here to check out all the sailing destinations we have explored so far.

We hoped you like the blog post and found useful information for yourself. If you don’t want to miss out on our next blog subscribe now to our newsletter or follow @whensailing on most social media platforms

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