The Mediterranean’s largest island sits amid Europe, Africa, and the Middle East. Over the centuries, this strategic position allowed Sicily to become Europe’s melting pot. The Greeks and Romans, and then the Arabs and Normans, all left their footprint, only to be followed by the French, Spanish, and Italians, creating a legacy of art and architecture that stands virtually unrivaled in Europe.
These disparate influences also seasoned Sicilian cuisine, and they can be traced back to the various cultures that have inhabited the island during the last two millennia. Greek, Arab, French, and Spanish accents spark the food. The Tunisians brought couscous, and Arab Muslims injected chili into the southern Italian menu via Sicily, and so on. It is even said that pasta may have been introduced to Italy and Europe by way of Sicily.
One way to understand how Sicilian cuisine fits into Italy’s diet is to work your way to the island starting from the rich northern cities. Take the train south from Milan to Sicily, and you’ll ride the shin of Italy’s boot down to the toe. On the journey, you will trade butter for olive oil, veal for swordfish, basil for mint, eventually landing in Villa San Giovanni. From this unremarkable port, the train cars trundle onto specially designed workhorse ferries that efficiently transport the carriages across the three-mile-wide Strait of Messina to land in Sicily.
And then you exhale. Suddenly the sun is a bit more unrelenting, and the mornings and nights start and end later. The pace, especially outside the main cities of Palermo and Catania, is slower. A full circumnavigation of the island will cover well over 500 miles, and the circuit can give you a sense of the differing regions and variety within Sicily.
For centuries, Messina has served as the western link for transportation between Sicily and the mainland. The gritty city is hard to avoid, but it is also the gateway to Taormina, the first important stop on a counterclockwise trip around the island.
Positioned on steep, cactus-covered cliffs vaulting above the sea, Taormina was founded in the fourth century BC. The town’s Greek fathers probably selected the location in part for the dramatic backdrop that steaming Mount Etna provided for a horseshoe-shaped theater. While Taormina feels like more of a resort than an archeological site today, its uniquely Mediterranean beauty remains unparalleled, inspiring writers from Goethe to D.H. Lawrence. You can easily see why with an afternoon stroll along the Corso Umberto I, a pedestrian-friendly thoroughfare leading past chic boutiques and soothing fountains to the Piazza del Duomo, the town’s 13th-century cathedral, and on to the majestically sited gardens of Villa Comunale.
The eastern coast of Sicily is dominated by Mount Etna, Europe’s highest and most active volcano, rising to almost 11,000 feet and snow capped for much of the year. You can take a jeep tour near the summit—volcanic activity allowing—or ride a regional train, the Circumetnea, that lumbers slowly around almost the entire peak, a 68-mile journey.
While Mount Etna’s fireworks have caused heartache over the years, the volcanic slopes are blessed with fertile soil, flush with groves of blood oranges and Bronte pistachios, apiaries worked by Sicilian black bees, and vineyards that tap the savory minerals of its ashen flanks. In fact, viticulture here dates as far back as 2,800 years. Sicily is Italy’s largest wine region—producing more, even, than all of Australia. Although historically most of it was not high quality, increasingly sophisticated bottles are emerging today.
The Circumetnea ends in Catania, a city originally settled by Greek colonists, and the lava flows of Etna have threatened the industrial city through the ages (many of the city’s buildings are even constructed from solidified lava!). While Catania is a perfunctory stop on a round-island tour, it’s notable as the origin for the classic Sicilian dish pasta alla Norma, which embraces two of the island’s mainstay ingredients, eggplant and tomato, for a hearty meal.
Rounding the southern tip of the island reveals a succession of vivid beaches and hilltop towns sprouting from the slopes of the Hyblaean Mountains. The towns here merit a closer inspection. In 1693, the southern corner of the island experienced a disastrous earthquake. Some 50,000 people were killed; dozens of towns were leveled. An ambitious reconstruction was launched, and in just 50 years, the towns were rebuilt, leaving behind a style that was nicknamed Sicilian Rococo.
The long southwest coastline of Sicily is less heavily traveled, but it possesses one of Europe’s most beautiful classical sites, the Valley of the Temples. The rebuilt structures are among the best preserved from Ancient Greece, and if you’re lucky to be here in spring, the almond trees sprinkled amid the Doric columns will be trimmed with pink blossoms. The temples sit at the edge of Agrigento, which was one of the most prosperous cities during the golden age of ancient Greece. Though badly scarred by Allied bombing during World War II, Agrigento has charismatic cobblestone streets, and nearby in San Leone are long beaches, making an overnight or two worthwhile.
As you round the western tip of Sicily, there are two local dishes you’ll encounter. In the quiet seaside town of Marsala, the richly colored namesake wine gets its due in chicken Marsala. The recipe’s roots may owe more to the British Empire than Sicilians—fortified wines like port and Marsala were sturdy enough to survive the journey to far-flung colonial outposts—but the dish remains a mainstay of Italian restaurants in America.
The nearby port city of Trapani, the main transport hub for shipping to Tunisia, is known for a wonderful twist on the traditional green pesto of Liguria. The recipe for pesto alla Trapanese still uses basil, but tomatoes take center stage, and instead of pine nuts, toasted almonds serve as the supporting player—a North African touch—ground together into a delectable paste and served over pasta.
Continuing along the north coast, we come to Palermo, Italy’s fifth-largest city—and one of its most cacophonous and multicultural. Fronted by the sea and wrapped by mountains, Palermo has seen an injection of capital that is allowing bombed-out neighborhoods from World War II to be revitalized, revealing many of the city’s Byzantine mosaics and frescoed cupolas.
Street food is ubiquitous, and often daring, in Palermo with arancine (fried rice balls) and chickpea fritters competing with spleen sandwiches and grilled sheep or goat intestines. In restaurants, a local staple served in the spring is frittedda Siciliana, a stew of vegetables starring artichokes, peas, and fava beans.
As you follow the coast back toward Messina, you’ll discover a septet of islands on the horizon: the Aeolian Islands. Among them, Stromboli is barely two miles wide and defined by its namesake volcano, which has eruptions as often as every 20 minutes. They are faint explosions that vault incandescent lava bombs into the air, accompanied by seductive wisps of vapor; it’s a spectacle at night.
The easiest island for an overnight stay is Lipari, the largest and most bustling of the Aeolians. Its narrow streets are lined with cafés and shops selling the island’s noteworthy exports, malvasia, a sweet, golden wine varietal, and capers. Restaurant menus here are heavy with seafood, and simply cooked swordfish will likely be spiced with capers, minced anchovy, and red pepper flakes—all ingredients that define the flavors of this magical archipelago.
David Swanson’s writing and photography has been featured in the pages of National Geographic Traveler, American Way, and the Los Angeles Times for more than 20 years. He served as President of the Society of American Travel Writers in 2018-19.