The best road trips in Sicily

At the crossroads of history, Sicily features Greek and Roman ruins as well as medieval and baroque towns that will delight you with their beauty. The largest island in the Mediterranean makes for a grand road trip destination, where you'll find beautiful blue waters along a rocky coastline, plus winding pastoral roads meandering through the hilly hinterlands near Palermo and up to the dark volcanic slopes of the testy Mount Etna.

If you want to explore the charming seaside villages, beautiful baroque towns and Greek and Roman ruins of Sicily, there's no better way than on a road trip. These can be done alone or joined together over several days. Here are my top tips on the best road trips in Sicily, including which inner village is serving the most delicious cannoli.

1. Around Mount Etna

Best road trip for adventurous wine-lovers
Start: Catania
Finish: Catania
Approximate distance: 162 km (100 miles)

You could circle Europe’s most active volcano in a day by car, but a longer trip gives you more time to appreciate the unique terroir of this microregion that produces some of Sicily’s finest wines. You’ll find unique stays in the small towns throughout the region, like Palazzo Previtera, a family-owned boutique hotel in Linguaglossa, or accommodations in the countryside with a cozy agriturismo or winery stay.

Also consider making space in the itinerary for a climb to the top of Mount Etna, or take the car as high as it can go to Rifugio Sapienza.

2. West Coast

Best road trip for families
Start: Palermo
Finish: Marsala
Approximate distance: 221 km (137 miles)

Heading west from Palermo, you’ll find some of the best swimming spots in Sicily, including the family-friendly resort town of San Vito Lo Capo and inspiring historic sights like medieval castles and fortresses.

First, stop by the temple of Segesta to see a remarkably intact 2000-year-old temple. If you’re outdoorsy, you can also try the trails at the Riserva Naturale dello Zingaro, or continue your journey towards Erice, a historic town perched atop the peak of Mount Erice and featuring an impressive fortress. Stop in Trapani, the largest city on Sicily’s west coast and your access point to catch a ferry to the Egadi Islands. Keep driving along the coast, and you’ll end up in Marsala, where you can tour the salt flats, relax on more sandy beaches and sample some sweet dessert wine.

Planning tip: You can skip the drive up the mountain to Erice by taking the cable car from Trapani.

3. Palermo to Agrigento

Best for small-town adventures
Start: Palermo
Finish: Agrigento
Approximate distance: 165 km (102 miles)

Leaving the commotion of Palermo behind you, start this road trip with something sweet by first stopping in the town of Piana degli Albanese, where Sicilians widely agree Extra Bar Petta makes the best cannoli on the island. Afterward, you can pass through the real Corleone to learn the sobering truth of the mafia and the inspiring story of the anti-mafia movement at CIDMA.

From Corleone, you can go east and make a detour to pay tribute to Old Blue Eyes in Lercara Friddi, the birthplace of Frank Sinatra's father. Or head west to Giuliana, where an incredible view of the southern part of the island is available from the old castle walls. You’ll finish this tour of small-town Sicily in Agrigento and Valle dei Templi, a sprawling archeological complex dating back to ancient Greece.

Local tip: No matter how you get to Agrigento, the famous Scala dei Turchei beach is always worth a visit, especially if you want to relax after a long day of sightseeing in the ruins.

4. Palermo to Catania

Best for coastal sightseeing
Start: Palermo
Finish: Catania
Approximate distance: 317 km (197 miles)

Heading east from Palermo, the beaches will get rockier, so be sure to make your first stop in sandy Cefalù, a charming seaside village and a popular vacation spot. Follow the coastal route to Milazzo, where you could catch a ferry to the Aeolian Islands; or continue towards Messina and consider going all the way to the point of Torre Faro, where you will be able to see mainland Italy across the Strait of Messina’s narrowest point, only 5km (3.1 miles) wide.

Follow the coast south to Taormina, where it’s worth finding a hotel on the low road near Isola Bella – like the Panoramic Hotel, which gives you a picture-perfect view of the island – and taking the cable car up to the mountainous city to enjoy the luxury shopping and Mount Etna views from the awe-inspiring Greek Theatre. On the way to Catania from Taormina, consider hopping off the highway and booking a guided hike to the summit of Mount Etna.

Planning tip: The fastest – but less scenic – way to make this trip would be to cut through the island. Although, it does offer a chance to see the medieval city of Enna, which played an important role in the island’s history.

5. Syracuse and the Southeast

Best for ancient and baroque gems
Start: Catania
Finish: Ragusa
Approximate distance: 170 km (105 miles)

Starting from Catania, follow the coastal road south to Syracuse and Ortigia, where you can wander the ancient ruins and stone quarries of the ancient city and the historic island that promises great nightlife on top of historic attractions. Keep going south, and you’ll reach Noto, one of the most highly praised towns in Sicily for the beauty of its baroque architecture. After a stroll around town, continue down the coast to the small beach town of Marzamemi for a little respite on the Ionian Sea.

Once you’re satisfied with the southeastern tip of the island, turn west to continue your baroque journey in the smaller towns of Modica and Ragusa, which are particularly well-known and sought-after gastronomy destinations, with an array of Michelin-star restaurants like the two-star Duomo being the prime foodie attraction.

Planning tip: The best way to enjoy one of the ancient Greek theaters outside of a daytime visit is to book a ticket to a performance. Just make sure to buy your tickets in advance.

Tips for driving in Sicily

Driving in Sicily is not for the faint of heart. The road culture is aggressive, and you will see other drivers pulling off daring maneuvers mid-gridlock. You will need a heightened sense of awareness and to proceed with extra care when driving in big city centers. Also, be prepared to find rough road conditions if taking shortcuts in rural hilly areas. You may have to stop for animal crossings.

If you're driving in small medieval towns, prepare yourself to navigate narrow and steep streets, and don’t put all your trust in the GPS. When in doubt, find a central place to park and go on foot if you can, especially if the area is marked Zona a Traffico Limitato (ZTL), which means you could be fined if you enter by car anyway. Look for the white circle with a red outline.