Sailing in Sicily: A 7-day itinerary

Sail in Sicily!

Only 2 miles off the tip of Italy’s ‘boot’, Sicily is the largest island in the Mediterranean. Its coastline is speckled with picturesque archipelagos that make it the ideal sailing holiday destination for your next yacht charter. Recently, some of GlobeSailors own charter advisors had the chance to charter a yacht in the Aeolian Islands. Their firsthand tips and experiences of Sicily have inspired this blog, and their pictures provide a unique perspective of the beautiful scenery. We hope this itinerary will help you make the most of your own yacht charter in Sicily, whether you’re exploring its history, tasting local dishes, or relaxing by the beach.

The Aeolian Islands are a particularly attractive sailing spot. As one of Sicily’s three archipelagos, the Aeolian islands are a group of seven volcanic islands that were added to the UNESCO World Heritage List in 2000 and are studied by geologists worldwide. According to old legend, these islands were named after a Greek God of the Winds, Aeolus, who could predict the weather from the shapes of the steam coming from the volcanos.

Day 1: Portorosa – Vulcano (approx. 20 nautical miles) 

You will begin your journey in Portorosa Marina in Eastern Sicily, which is easily accessible by train from Catania, Palermo, or Reggio Calabria airport. The latter of which is accessible directly from over 15 European cities. The sea here was awarded a Blue Flag by the Foundation for Environmental Education (FEE), for meeting high standards of water quality and services.  

On the first day of your yacht charter in Sicily, head for Vulcano – the southernmost Aeolian Island! Named after the Roman god of fire, Vulcan. This island is famous for its gaping craters, relaxing mud baths, thermal springs and black sand beaches. Mud baths have been around for thousands of years and can relieve stress, joint pain, and even some skin conditions. Take this opportunity to unwind and relax before you set off again to discover the ‘horse’ grotto, a rocky nook to the west of the island with a boulder on the end resembling a horse’s head. Or hike to the great La Fossa crater and marvel at the luminous yellow ground thanks to the sulphur deposits!

Day 2: Vulcano – Filicudi (approx. 20 nautical miles) 

Depart from Vulcano and head towards Filicudi, a stunning island off the northeast coast of Sicily. A rocky gem, unspoilt by tourism and brimming with nature, Filicudi is home to eight extinct volcanoes. Explore the scenery by hiking to the abandoned village of Zucco Grande and then to Fossa Felci, a mountain in the island’s center. You can also explore the prehistoric village of Capo Graziano, which dates back to 1800 BC!

Day 3: Filicudi – Alicudi (approx. 13 nautical miles) 

Continue your sailing holiday in Sicily, and sail to Alicudi, the smallest and least populated of all the Aeolian Islands. It is in the peninsula’s bluest sea and known as the island of a thousand steps. Explore the rocky beach of Spiaggia Bazzina, or visit the Rock of the Galera in the west of the island, which has been said to resemble the head of a dragon.

After that, why not don your hiking shoes and hike straight from the port up to Filo dell’Arpa, a mountain 675m (about twice the height of the Empire State Building) above sea-level with stunning 360° views of the north-western coast of the island. After building up an appetite, enjoy a traditional dinner at Bar L’Airone, one of the only restaurants on the island!

Day 4: Alicudi – Salina (approx. 26 nautical miles) 

Raise anchor and set off to Salina, the greenest and second largest island in the Aeolian archipelago! It is known for its luscious natural reserve that accounts for over half the island.

It is also home to an abundance of vineyards, where a high-quality Malvasia (a wine grape typically grown in Mediterranean regions) has been produced for centuries. There are narrow streets, and beautiful pebbled beaches. You can visit the town of Santa Marina, where you can browse in various shops, restaurants and even a museum of wine! Why not go and see Fossa delle Felci or Monte dei Porri, the two volcanoes on the island which have been dormant for over 13,000 years!  

Day 5: Salina – Stromboli (approx. 20 nautical miles) 

For your fifth day of your yacht charter holiday, sail to the volcanic island of Stromboli! Stromboli is the most northeastern island in the Aeolian archipelago and is so named after the mountainous active volcano on the island that reaches more than 920m (about 3018.37 ft) above sea level. Admire the great rock of Strombolicchio, and stop for a snorkel in the crystal blue waters.  

Day 6: Stromboli – Lipari (approx. 24 nautical miles)

Lipari is the largest of the Aeolian Islands, boasting beautiful sites such as ancient volcanoes, hidden beaches, hiking trails and little coves. This island is brimming with heritage and culture, visit the Cattedrale di San Bartolomeo, a church that is perched at one of the highest points of the island. Why not explore the two main villages of the island, Marina Lunga and Marina Corta which are both full of picturesque shops and restaurants serving authentic local cuisine. You can also hike to the best viewpoint on the island, Belvedere di Quattrocchi and admire the turquoise waters of the Tyrrhenian Sea. 

Day 7: Lipari – Portorosa (approx. 22 miles) 

Return to Portorosa on the last day of your sailing holiday, don’t forget to take one last morning swim in the sea before you pack up and disembark! Spend your final evening in Portorosa, soaking up the last of the Sicilian sun after your relaxing yet memorable week on the water.  Ensure you contact your GlobeSailor charter advisor before your holiday to arrange your return airport transfer.

Interested in more?

Embark on the holiday of a lifetime, contact one of our expert charter advisors today to organise what is sure to be your favourite holiday yet!