This harbour 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-largest city on the island and considered the gateway to Sicily. But while it often goes unnoticed by many visitors, with its mix of Norman and Gothic architecture, vibrant local festivals and cheerful, welcoming residents, it deserves to be a stop on any Sicilian road trip.

Visit the 60-metre-high bell tower with its astronomical clock. At midday each day, its figures act out scenes from the city’s history. Stroll along 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, at the island’s furthest point. 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 chance you might never want to leave. Despite its popularity with tourists, it still feels like 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 really is a place made for the photo album.

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

Then walk out to ‘La Rocca’, a huge rock sitting above the town with exceptional views across Cefalù. As the sun sets, stroll along the seafront promenade and treat yourself to an Aperol spritz. And keep an eye out for filming locations from Cinema Paradiso, which was filmed here.

Palermo has a reputation for a certain gritty edge, but don't be put off — it has far too many treats, mostly culinary, 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 full of charm and personality, this is a city of winding streets, Byzantine mosaics, arching domes and boisterous markets. It’s noisy, seductive and utterly unique.

This Sicilian road-trip stopover is all about the food: make sure you explore the city’s amazing food 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 mosaics — and the Moorish Norman Palace. Once you’re done, go back 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 it became a successful trading hub. Today, Marsala is a charming and laid-back stopover on your Sicily road-trip itinerary.

Wander its gleaming 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’d 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, isn't 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 trip back in time 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 infamous 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 thoroughfare of the old town, lined with trattorie 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 Sicilian 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. Be awestruck by the ancient-world ruins of the Parco Archeologico della Neapolis. Take a boat trip around the Porto Grande, where the Syracusans and Athenians fought 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 the local food, just as unforgettable as the city itself.