Sicily doesn’t always make it on to everyone’s Italy itinerary, but it should. Maybe not the first trip since people surely want to explore the big cities of Rome, Florence, and Venice, but Sicily should definitely be explored on later trips. And the best way to see Sicily is, by far, by car. Not only is it more convenient than a train trip through Sicily, the island is notorious for having a poor train system, but driving through the island also means taking detours from your original itinerary, exploring the coastline, and climbing up into the hills. Not to mention, you don’t have to be constantly shifting your luggage around! Hotels in Sicily are very reasonably priced—especially during shoulder or low season when there are fewer people but yet still beautiful weather. Allow yourself at least a week to take in this fantastic Sicily itinerary.
To start your Sicilian roadtrip, fly or take a ferry to Palermo, the island’s capital, which is a gorgeous metropolis on the north coast of the island. Known for its beautiful Baroque architecture, amazing cathedral, and delicious Capo food market, Palermo is a gem worth exploring for a couple of days. Easy day trips can be made to Monreale with its Arab-Norman architecture, as well as Cefalù, a beautiful beach town with fantastic castles and ancient city ruins.
From Palermo, make your way west to Trapani, stopping off for an afternoon in San Vito Lo Capo, a quaint town on a gorgeous peninsula that is overtaken by sunbathing Italians during the month of August. In Trapani, you’ll enjoy a lovely pedestrian city center, as well as salt marshes and beautiful windmills. Also visit nearby Erice, a hilltop town reachable by cable car known for its ancient city walls; Segesta and its Greek ruins; and Marsala, known for its namesake wine.
Continue along Sicily’s southern coast in order to reach Agrigento, famous for its enormous archeological site, Valley of the Temples. There, you’ll be able to explore seven enormous Greek temples—the best-preserved of their kind outside of Greece. The city of Agrigento, perched high above the Valley of the Temples, is charming with its narrow streets, store-lined walkways, and steep hills.
Keep heading east in order to reach Siracusa, but stop in at Gela for a day at the beach or Noto for a look at its stunning Baroque cathedral. When you reach Siracusa, explore the oldest city in Sicily, heading to the Ortigia island/neighborhood to get a true feel of the city: the cathedral, Archimedes Square and the Fountain of Diana, and Castello Maniace. Also check out the Siracusa archaeological park—namely the Greek theater and the acoustic wonder of Dionysius’ Ear.
Head north up Sicily’s east coast, driving past the still-active Mount Etna, in order to reach Taormina, the Pearl of the Mediterranean, which clings onto a mountain top overlooking the ocean. Stroll through the quaint city center and check out the Teatro Greco. Giardini-Naxos, located at the foot of the mountain, is a beautiful spot for a beach day.
Fly out of Catania or take a ferry from Messina to the tip-toe of Italy to continue up the boot to explore the rest of the country. Of course, this itinerary can also be followed in reverse! What are you waiting for? It’s time to hit the road!