This harbor city on the north eastern tip of Sicily is separated from Italy’s boot by the Strait of Messina, a body of water inhabited by mythical sea monsters, according to legend. 

Messina is the third biggest city on the island and considered the gateway to Sicily. But while it escapes the notice of many visitors, with its mix of Norman and Gothic architecture, vibrant local festivals, and cheerful and welcoming residents, it deserves to be a stop on any Sicily road trip.

Visit the 60 metre high bell tower with its astronomical clock. At noon each day, its figures act out scenes from the history of the city. Stroll the Viale Italia, the walkway and boulevard running above the city. At the end, you’ll be rewarded with stunning views across the city and harbour. 

Before heading on to your next destination, drive the beautiful road out to Torre di Faro, the furthest tip of the island. And be sure to try the local delicacy: swordfish.

Against the backdrop of the soaring Madonie mountains, the unfairly beautiful Cefalù is a risky road trip stop, there’s every danger you might never leave. Despite its popularity with tourists, it retains the allure of an authentic little fishing village.

With its gorgeous beaches and Arab Norman cathedral decked in mosaics, its medieval squares, cobbled streets, and honey coloured buildings, Cefalù truly is a destination designed for the photo album.

Continue your Sicily road trip from Messina to Cefalù. On arriving, first relax with a cold granita down by the picturesque port. Visit the jewel like cathedral, it’s a must for any culture lover.

Then take a hike out to ‘La Rocca’, a giant rock sat up above the town with exceptional views over Cefalù. As sunset arrives, stroll along the seafront promenade and treat yourself to an Aperol spritz. And keep your eyes peeled for filming locations from Cinema Paradiso which was shot here.

Palermo has a reputation for a certain gritty edge, but don’t be put off. It has far too many treats mostly of the culinary sort, to miss out on.

Its eclectic mix of cultural influences, both European and North African, is evident in everything from its architecture to its cuisine. Hectic but with a distinct charm and lots of personality, this is a city of winding streets, Byzantine mosaics, arching domes, and boisterous markets. It’s noisy, seductive, and unique.

This Sicily road trip stopover is all about the food: make sure to explore the city’s amazing culinary scene in depth. Visit markets like Vucciria and try treats like panino alla milza, pane e panelle, and skewered octopus.

For a real culture-hit, head to the cathedral, the glinting Palatine Chapel, entirely covered in glittering gold mosaic and the Moorish Norman Palace. Once you’re done, return to sampling the local delicacies: food is one of the things Palermo does best.

While most famous for its amber coloured wine, Marsala is also a town with a rich history as an important port and stronghold.  

In the past, Marsala was a thriving Roman colony. With the arrival of the Arabs, a successful trading hub. Today, Marsala is a charming and laid back stopover on your Sicily road trip itinerary.

Wander its shining marble streets, past elegant townhouses, and relax in delightful piazzas. Eat great local food and enjoy life’s simple pleasures. Low key but lovely. 

Explore the beautiful Baroque old town. Visit the Baglio Anselmi, the town’s cathedral. Learn about the history of the town at the Complesso Monumentale San Pietro. The Archaeological Museum is also worth a visit with its most intriguing relic: a Phoenician boat.  

Of course, you should also do some wine tasting, it would be rude not to. Finally, if you have time, you could take a boat trip to the gorgeous Egadi Islands.

While Agrigento, a modern metropolis, is not the most captivating of cities, this stop on your Sicily road trip itinerary is about something far more ancient and mythical. 

Just behind Agrigento are the ruins of the ancient city of Akragas in the Valley of the Temples: the best-preserved Greek Temples in the world, perched on top of a half-mile-long ridge and surrounded by olive groves and almond orchards. Never has the ancient world felt so alive.

After returning from your time travel trip back to Ancient Greece, you could pay a visit to Villa Romana del Casale with its elaborate mosaic murals that include the famous female athletes with the notorious nickname, ‘The Bikini Girls.’

 In the evening, explore the centre of Agrigento, a charming medieval old town with a lively nightlife: beautiful palazzi, majestic churches, and the Via Atenea, the main artery of the old town, lined with trattorias, serving delicious local food, and bustling bars.

Cicero called Syracuse “the greatest Greek city and the most beautiful of them all.” He wasn’t wrong. On this waypoint on your Sicily road trip, you’ll encounter unspoilt historic beauty at every turn. 

Ancient Greek ruins emerging from citrus orchards. Cobbled lanes leading you to Baroque piazzas. Stately churches and golden buildings tumbling towards the turquoise sea. This city will transport you back in time.

Visit the Greek Theatre and the Ear of Dionysius. Find yourself awe-struck at the ancient world ruins of the Parco Archeologico della Neapolis. Take a boat trip around the Porto Grande where the Syracusans and Athenians battled in 413 BC.

Then swap ancient culture for more modern offerings with a wander around Ortygia, a hip and sophisticated hub joined to the mainland by a bridge.

Discover artisan boutiques, puppet shows, chic new wine bars and pebbly beaches where fishermen still mend their nets. And sample local food just as unforgettable as the city itself.