Sail Northern Sicily and the Aeolian Islands

Famous for its beautiful coastline, active volcanoes, delicious cuisine, wine and fascinating history, Northern Sicily and the nearby Aeolian Islands make an unbeatable charter destination, easily accessible with bases on Sicily itself and at the mainland port of Tropea.

What makes Sicily an even better sailing holiday destination is the flexibility it provides. Extend your cruise west to the Egadi Islands and Siciiy's south coast, or east to Messina and beyond. Or even consider a Sicily circumnavigation.

Northern Sicily

Sicily is Italy's largest island with a land area of 25,706 sq km (9,925 sq miles), as well as being also the largest island in the Mediterranean Sea.

Because of its strategic location (latitude 38° north), Sicily has been invaded countless times over the centuries, by the Greeks, Phoenicians, Romans, Arabs, Normans and Spaniards. Each occupier left behind their cultural influences that have blended to give Sicily its own distinctive personality, in its architecture, cuisine and customs.  A visit to Sicily is certainly an experience to treasure, and that's without taking account of all the great sailing to be had. 

There are bays and ports well worth stopping into all around the island of Sicily. Many charterers do however restrict their Sicilian sailing holiday to the northern coast, visiting the city of Palermo, historical Cefalù and delightful Portarosa. It's just a short sail from here to the Aeolian Islands and a quite differnt world. 

The Aeolian Islands

Rising out of the Tyrrhenian Sea some fifteen miles off the Sicilian coast, the Aeolian Islands - Lipari, Salina, Stromboli, Vulcano, Panarea, Filicudi and Alicudi — with their black beaches of volcanic soil, and dazzling clear light, have everything to make your yacht charter an unforgettable experience.

The history of this UNESCO World Heritage Site is recorded back at least 5,000 years, and traces of human presence can be found in the form of prehistoric villages, ruins, excavations, pottery and tools. The setting is a volcanic one, “Fire above and below” is how one writer describes the ambience, "baking under the constant glare of a Sicilian sun."

Colourful fishing boats line lively ports, filled with charming cafes, bars and restaurants.  While the islands’ interiors offer the most varied and contrasting landscapes and scenery, the crystal clear water in sheltered bays and coves, volcanic activity, isolated reefs, starkly-painted houses and archaeological sites are unmatched for beauty and drama.  The food and wine are simply extraordinary, and some of the islands offer the rare experience of an almost vehicle-free environment.

Sailing here is away from it all, detached from the highly-populated tourist tracks. Although Italians have been holidaying in the Aeolian islands for centuries, the rest of the world is only just now awaking to their charms.

Combine your trip to the Aeolian Islands with a tour of Sicily, or travel to the 16th Century Calabrian town of Tropea, and use that as your base for this great Mediterranean charter holiday option. 

Our client reviews about charter sailing in Italy

We had a great time in the Aeolian Islands, and I highly recommend them as a destination. The beauty is that the islands each have a different character and are close to each other. The longest ‘passage’ is about 10 miles, and some are a lot shorter. Two of the largest islands, Vulcano and Lipari, are only 800m apart, but very different! The marinas are well located and were reasonably priced (€70-100 per night) and at Panarea there are only moorings but for €70 you also get a 24/7 water taxi service which was perfect. We found mid / late July to be superb.
David, New Zealand, Aug 16th, 2019
Rating: 5 / 5
We found the boat to be nicely designed and very comfortable. The sails were near new and a treat to sail with. The highlight destination was Capri where because of unsettled weather we stayed in the marina. We found a brilliant restaurant in Ana-Capri and enjoyed strolling the narrow streets. San Michelle villa was delightful. Service was 10/10. Mario at the marina went out of his way to help us with ideas advice and making sure we wanted for nothing. Peter, New Zealand, Oct 24th, 2018
Rating: 5 / 5
The cat performed well with everything working as expected. The only issue was batteries not lasting a night and having to run an engine both in the morning and again in the late afternoon when sailing and not motoring. Sails were easy enough to hoist and the electronics worked well. Lipari was a great spot to stop with a nice town to explore. But the nicest island I found was Panarea. Less tourists with very friendly locals. James, Australia, Jul 22nd, 2018
Rating: 4 / 5
The Aeolian islands are a beautiful part of the world with many highlights. The standout was watching Stromboli erupt at night from nearby offshore. Sail Connections service was as always excellent. Russell, Australia, Jul 16th, 2018
Just a quick note to say we had a fabulous holiday and fantastic charter. The boat was perfect and the skipper Salvo and hostess Lucia were excellent could not fault anything. Salvo took us to some amazing places, always had our comfort and safety in mind, and was a lovely guy, Lucia was an amazing cook we ended up having most of our meals on board she was so good, also great company and very friendly and helpful. Everyone at North Sardinia Sail were also helpful and very friendly. Tony, Australia, Aug 31st, 2016
I just wanted to say thank you. We had a great time sailing though Italy and we appreciate your help putting that together. We had a blast on the trip! Cilento is beautiful and I'm really glad we went south before heading across the bay to Capri and Amalfi. Happy to share more stories/insights from the trip so you can help other explore this beautiful region, Thanks again. John & Leah, USA, Sep 30th, 2015
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

Get in Touch

Related Blog Posts

  • Charter a Gulet: Luxury Cruising in Classical Style

    Charter a Gulet: Luxury Cruising in Classical Style

    For your next sailing holiday, particularly in the eastern Mediterranean but in some other surprising places as well, consider chartering a gulet. Today's gulet is now a modern charter boat built for a unique vacation experience enjoyed in complete passenger comfort and luxury living aboard.

  • Charter Sailing Sicily, including the Egadi Islands

    Charter Sailing Sicily, including the Egadi Islands

    On our 2018 Mediterranean charter we made a spot decision to spend time in Sicily. We chose to sail out of Palermo, a convenient base for going east to the Aeolian Islands or west and south the same distance to the Egadi Islands. But the main factor was a near-new Oceanis 38 available just 3 days out from charter.

  • A Fleeting Sailboat Tour in Corsica and Sardinia

    A Fleeting Sailboat Tour in Corsica and Sardinia

    After an uneventful passage from Villefranche-sur-Mer to Corsica, a 95 nautical mile passage to the port of Calvi, we had nine days to deliver our boat to its Ajaccio base. Just enough time to explore Corsica’s west coast and visit northern Sardinia, as long as we kept moving

  • Italy under Sail: The Gulf of Naples and Amalfi Coast

    Italy under Sail: The Gulf of Naples and Amalfi Coast

    If a Mediterranean yacht charter is on your bucket list, you are certainly spoiled for choice. A sailing vacation out of Naples provides some of Europe’s best holiday experiences.

  • Italy under Sail: Sicily & the Aeolean Islands

    Italy under Sail: Sicily & the Aeolean Islands

    Sailing the coast and islands of Italy will transport you to another time. Some of the places you visit will claim to be the oldest trading ports in the world - destinations that date back to antiquity.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.