For a good sampling of Sicily, plan to visit a mix of big cities (Palermo, Siracusa); smaller towns (Ragusa, Trapani, Taormina, Cefalù); and striking sights in the countryside (Mount Etna, ancient temples and theaters, the glittering mosaics at Monreale Cathedral). On a quick visit of just a few days, home-base in Taormina or Catania and make strategic side-trips to Siracusa and Mount Etna, then spend a day or two in Palermo.
With more time, consider adding your choice of other towns: Agrigento (with its remarkable ancient temples), additional time in Siracusa (for its ancient sites and delightful urban bustle), Ragusa (for its low-key hill town ambience), Trapani (a pleasant west coast town with an array of tempting side-trips, from salt flats to hill towns to offshore islets), and the beach town of Cefalù. For most travelers, the best plan is to rent a car — but be prepared for the often challenging Sicilian roads, especially in cities.
The island’s cuisine — which is distinctly different from mainland Italy’s — is, like Sicily, a unique mix of cultural influences. Choosing between eggplant pasta and fish couscous on the same menu, it’s clear that you’re at a crossroads of Europe and Africa. And some of the best food is also the cheapest. Sicily is renowned for its street food.
Try an arancina (deep-fried saffron rice ball), panelle (chickpea fritters), sfincione (rustic, Sicilian-style “pizza”), polpo bollito (a boiled mini-octopus), and — if you dare — pani ca’ meusa…the famed spleen sandwich. To sample several items in one go, just wander through one of the characteristic street markets in Palermo or Catania…or join a street food tour.
Party with the Sicilians.
On this island of very tight-knit communities and fierce local pride, there’s always some big festival going on. Most towns celebrate their patron saint’s day by processing through the streets with an elaborate float (or several). Other celebrations fill a more specific niche. I happened to be in the pristine town of Noto during their biggest party of the year, the Infiorata di Noto. An entire street — several blocks long — was filled with gigantic murals, delicately constructed of flower petals. And when I was in nearby Ragusa, the townspeople were celebrating the native Ragusano cheese.
The town square hosted cooking demonstrations, and every restaurant in town was highlighting a special cheese-forward dish. While I enjoy the serendipity of just stumbling onto Sicilian celebrations, it’s smart to do some homework, find out what local festivities might be going on nearby, and make a point to drop by.
Bone up on ancient history.
In antiquity, Sicily was called Magna Graecia — “Greater Greece” — for the many Hellenic city-states that colonized the island. Ancient Syracuse (today’s Siracusa) was one of the most powerful city-states on the Mediterranean. Sicily was also an outpost of the mysterious Carthaginians, who were almost entirely wiped out by the Romans. And all of these civilizations left behind world-class artifacts. Scattered across Sicily are some of the best ancient Greek temples and theaters anywhere outside of Greece: the Valley of the Temples at Agrigento; Europe’s largest archaeological area at Selinunte; and the theaters in Taormina, Siracusa, and Segesta.
The cathedral in Ortigia (Siracusa’s old town) is actually built upon the still-visible columns of a fifth-century B.C. temple. And deep in the remote interior of Sicily is the Villa Romana del Casale, with some of the world’s best-preserved floor mosaics. If you love ancient sites, Sicily will blow your mind. If you don’t…there’s no better place to start.