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I hadn’t really thought about it before I visited, but Sicily’s remarkable and consequential history should be obvious. Much of the history of Europe is the history of the Mediterranean Sea. As a large island right in the middle of the Mediterranean, Sicily was strategically vital at least from the time of the ancient Greeks through World War II. Some of the island’s oldest signs of human habitation are cave paintings dating to around 8000 B.C.E. In subsequent millennia, Sicily was settled by the Phoenicians, Carthaginians, Greeks, Romans, Germanic tribes, Byzantines, Arabs, and Normans. Each civilization left its mark, creating unique layers of history that you can still see today.

  1. Palermo
  2. Cefalù
  3. Agrigento
  4. Siracusa
  5. Taormina


I arrived in Palermo, on Sicily’s northwestern coast, on a Monday afternoon. With my family, I drove into town and set out to explore the city. A guide took us to some of the city’s most important sites, including Santa Maria dell’Ammiraglio, a Norman church featuring beautiful mosaics; Chiesa di Santa Caterina d’Alessandria a baroque church with an impressive cloister, old convent, and pasticceria offering deliciously fresh cannolis; the Fontana Pretoria (Fountain of Shame), built in Florence in 1554 and transferred to Palermo twenty years later; and the cathedral. We ate dinner on the Piazza Bologni; the food was uninspiring, but the setting was delightful.

Interior of the Chiesa di Santa Caterina d’Alessandria Interior of the Chiesa di Santa Caterina d’Alessandria

We began the next morning with a tour of the Norman Palace. The palace itself was impressive, and there was a neat historical museum, but the true highlight was the Cappella Palatina (Palatine Chapel). Decorated with intricate mosaics—the subjects are Christian but they show a clear Arab influence—and featuring a gorgeous muqarnas ceiling carved from wood, the small chapel was one of the most beautiful I’ve ever seen.

Inland from Palermo is the town of Monreale. Monreale’s cathedral was completed in 1267 and remains one of the world’s greatest examples of Norman architecture. While Monreale Cathedral is much larger than the Cappella Palatina and is certainly impressive in its own right, I found I preferred the more intimate and intricate beauty of the smaller chapel. However, it was certainly worth it to walk the terraces for great views back towards Palermo and the sea. The cathedral’s cloister also features numerous ogival arches and columns with detailed carvings.

The cloister of Monreale Cathedral The cloister of Monreale Cathedral

We ate lunch at Bricco E Bacco. The waiter didn’t speak much English, but he made it clear that he recommended a certain beef cut. The restaurant is known for its meat, largely due to its relationship with local butchers, so we followed the waiter’s advice. The beef came on a sizzling hot pink salt platter, covered in bubbling butter and herbs. It was fantastic.


From Monreale, we drove on Cefalù, a seaside town on Sicily’s northern coast. We wandered Cefalù’s streets, seeing the old city gate, a medieval laundry, the pier, and the cathedral. After a happy hour drink on a deck overlooking the ocean, we continued on to Relais Santa Anastasia, a winery in the hills above Cefalù that also functions as a small hotel. The winery is absolutely beautiful, and its restaurant provided an excellent dinner and tasty Sicilian wines.

Sunset from Relais Santa Anastasia Sunset from Relais Santa Anastasia

In the morning, we hiked Rocca di Cefalù, the massive rock formation looming above the town. The serpentine trail zigzags among Greek and Byzantine ruins before culminating in a Norman castle at its peak. The views in every direction were incredible. We enjoyed the vistas and the history for a while before returning to town for lunch. Then we visited the nearby hill towns of Pollina and Castelbuono.

Pollina is tiny, but its summit offers great views of the surrounding area. It also features the Museo Della Manna, one of the odder museums I’ve ever visited. Dedicated to manna, a sweet substance derived from the sap of ash trees, the museum features a few small exhibits on manna’s history and extraction process. It also has a number of products, including cookies, lotions, and liquors, made from manna. The custodian spoke no English, so we conversed primarily in French.

Castelbuono is larger than Pollina, but it doesn’t offer much more in the way of sightseeing. Its main attraction, Museo Civico di Castelbuono, is mostly forgettable; there’s a bit of interesting history and some strange art installations. We had a lovely happy hour on the town’s Piazza Margherita at Naselli, where our waiter was extremely helpful and friendly and invited us back for gelato made from ingredients grown and produced entirely on the island of Sicily (they use manna instead of sugar). After dinner we returned for dessert and conversation and sat for a long time chatting and sampling the local gelato.


The next day began with a long drive south across the island to Agrigento. We met a guide who took us to Museo Archeologico Regionale Pietro Griffo, Agrigento’s archaeological museum. The museum contains a large collection of Greek and Roman artifacts, including a massive statue of Zeus, reconstructed from the ruins of an enormous temple that featured several of the statues along each of its walls.

Agrigento’s real draw, though, is its collection of Greek temples. At least twelve once stood along the city’s southern wall. The temple of Zeus is almost entirely gone, though the remnants of its foundations give you some idea of how gigantic it must once have been. Instead, the tour of the temples focuses on the three best-preserved temples: the Temple of Juno, Concordia, and the Temple of Hercules. Built from sandstone rather than marble, each is impressive, but Concordia is undoubtedly the most splendid. It’s often regarded as the best-preserved Greek temple outside of Greece, and perhaps the second-best preserved anywhere.

Concordia Concordia

We departed the lovely Santa Anastasia in the morning for another day of ancient history. We began at Morgantina, the site of a Greek city. It’s still an active archaeological dig, so visitors can’t wander the city center, but you can get a good view and walk through some of the ruins of the outlying homes. Then we stopped at the Museo Archeologico di Aidone, the archaeological museum in the nearby town of Aidone, which contains many of the artifacts recovered from Morgantina. My favorite was the stunning and rare Hades head, which, like a few of the other artifacts, had been recovered after years of legal wrangling from American museums that had purchased them from unsavory art collectors.

The Hades head at the museum in Aidone The Hades head at the museum in Aidone

From Aidone we drove to Villa Romana del Casale. We knew it was a Roman villa from around the fourth century C.E., but we didn’t know quite what to expect. It turned out to be one of the most amazing historical sites I’ve ever visited. The sprawling villa is huge; simply constructing it at the time must have been a major undertaking. But its most remarkable feature is that the floor in every room is an intricate mosaic, each a work of art in its own right. The mosaics are very well-preserved and are perhaps the richest collection of Roman mosaics in the world. The villa was occupied into the Middle Ages, but a landslide covered most of the building in the twelfth century, and it was mostly forgotten. When the site was excavated in the mid-twentieth century, many of the mosaics remained in excellent condition. Our guide took us through each of the sixty rooms of the house, explaining their functions and describing the features laid out in tile in their floors.

A mosaic at the Villa Romana del Casale A mosaic at the Villa Romana del Casale


We departed the villa as it was closing for the evening and drove on Syracuse, on Sicily’s eastern coast. Much of Syracuse is rather unremarkable, modern, urban, and not particularly pretty. But the island of Ortigia has, in recent years, become a bustling maze of shops, restaurants, hotels, and historical sites. We checked into our hotel and strolled up to the Temple of Apollo, the ruins of a large Greek temple, got some gelato, and went to bed.

In the morning, Lauren and I set out to explore Ortigia. We visited the statue of Archimedes, who held off a Roman siege of Syracuse for years before being killed during the invasion. We bought a seltz, a refreshing drink made from salt and sparkling water (and, in our case, lemon juice and lemon granita) at a stand on the Piazza Emanuele Pancali and sipped it as we walked through the market on the Via Emmanuele de Benedictis. We walked along the charming Via Cavour, lined with intriguing shops, and had a delicious pizza lunch.

We visited the cathedral, which is a microcosm of Sicily’s history. A Greek temple was constructed on the site of the cathedral around 480 B.C., and the first church there was built by the Byzantines in the sixth century A.D. Sicily’s Arab rulers probably used it as a mosque during the ninth century. During the twelfth century, the Normans built a grand façade, which was unfortunately destroyed in a major earthquake in 1693. The current baroque façade was added during the eighteenth century. The columns of the Greek temple are still visible as components of the cathedral’s exterior walls, and one of the columns still bears an obvious crack from the earthquake.

After lunch we ventured into Syracuse’s new town, much less charming than Ortigia. Our destination was the Catacombe di San Giovanni, a series of tunnels carved into the limestone by the Greeks for use as cisterns, which were subsequently repurposed by early Christians as a burial site. The catacombs were a little creepy and interesting to see, but the tour was subpar.

It happened to be my mom’s birthday, so in the evening we boarded a small sailboat and embarked onto the Ionian Sea. We cruised around Ortigia as it was draped in the oranges and yellows of a spectacular sunset. We didn’t see any dolphins, but did spot a flock of flamingos flying south towards Africa. Then we returned to Ortigia, where we anchored off of the island and enjoyed a birthday dinner.

Sunset behind Ortigia Sunset behind Ortigia

The next day, we drove south from Ortigia along the Vendicari Nature Reserve. We’d been told that the Reserve contained some interesting ruins, but we had trouble finding them. We continued a little further south and spent the morning lounging on the Mediterranean Coast at the Agua Beach Resort. Then we drove into a Noto, a town in the hills above the coast. Noto was destroyed in the earthquake of 1693, and, rather than rebuild, the residents erected a new town a few miles away. It was exquisitely laid out, and the entire city is a monument to baroque architecture and urban planning, full of stone streets, churches, and palaces.

Upon returning to Syracuse, we visited some of the shops we hadn’t seen yet, including an artisan who paints on papyrus made from locally grown plants. Then we strolled down the waterfront, watched a gorgeous sunset, and grabbed a happy hour drink.

The following morning we woke up and met Maurizio, chef at the local restaurant Macallè Sicilian Bistrot. Maurizio took us on a tour of the market, where we purchased some fish, vegetables and other accouterments. We also visited Borderi Gli Artisti, a restaurant and charcuterie on the market. Maurizio selected a delicious plate of meats, cheeses, and breads for us as well as a bottle of wine (it was awfully early, but still good). Then we went to Macallè, where Maurizio taught a cooking class for us. We made a salad, a pasta dish, and fish.

Stuffed to the bursting with amazing Sicilian food, we took a taxi out to the Parco Archeologico Neapolis, Syracuse’s archaeological park. We saw an ancient quarry, the Greek theater, and the Roman amphitheater. Then we visited the archaeological museum, an enormous building full of prehistoric, Greek, and Roman artifacts.

The beach below Taormina The beach below Taormina


Before leaving Syracuse the next morning, we visited Castello Maniace, the fortress at Ortigia’s southern tip that has guarded the city for centuries. Then we drove north to Taormina. Nestled in the hills between Mount Etna and the coast, Taormina is incredibly beautiful.  We checked into our hotel and walked down the hill to the beach, where we relaxed and enjoyed the water, though it was still quite cold. We returned to town and visited Teatro Antico, Taormina’s Greco-Roman theater. Originally constructed by the Greeks during the third century B.C.E., the theater was largely rebuilt by the Romans. Today it’s still used for stage and musical performances. Spectacularly located beneath Mount Etna, the theater offers breathtaking views of the volcano and the Ionian Sea.

Teatro Antico di Taormina Teatro Antico di Taormina

From the theater, we explored the city. Taormina is an ancient town. The area has been inhabited since prehistoric times. The Greeks founded the nearby town of Naxos in 734 B.C.E. The nearby town of Tauromenion was large and prosperous by 345. The city contains ruins from the Greek, Roman, Byzantine, and Norman eras. We ambled down the Corso Umberto, Taormina’s main street, which is lined with shops and restaurants. Many of them cater to tourists, but a significant portion offer unique wares. We ate dinner at Osteria RossoDiVino, and it was one of the best meals we’ve ever had. We picked freshly caught fish from the day’s selection and chose the method of preparation (one baked in a salt crust, then painstakingly extracted and filleted by our waiter, the other covered in breadcrumbs and grilled with lemon, salt, and herbs). We also had a fantastic pasta dish and some delicious wine.

The next morning, a guide met us at our hotel and drove us up the slopes out Mount Etna. At the Rifugio Sapienza we caught a cable car that took us further up the slopes. Then we proceeded to explore the surrounding volcanic formations. It was a frustrating experience; while some of the features were interesting and there were some good views, the hike was hot and dusty, and there was a bus that offered rides to our destination. We couldn’t summit the mountain, as recent volcanic activity made it too dangerous. However, we were able to hike to the site of one of the recent lava flows, where the rocks were so hot that they threatened to melt the soles of our shoes, and we could glimpse the red molten lava. We returned to Taormina for a walk through the city’s beautiful communal gardens, a granita, and a pizza dinner.

Lava cools on Mount Etna Lava cools on Mount Etna

Our time on Sicily was rapidly coming to an end. The next day—our last full day on the island—we visited the Aeolian Islands. A UNESCO heritage site, the islands had repeatedly been described to us as spectacularly beautiful and unmissable. The opposite was true. We started on Lipari, the largest of the islands. We visited the castle and archaeological museum, which was interesting but much less impressive than many of the museums and historical sites we’d already seen. After eating lunch, we took a boat to Vulcano, as our guide had recommended it as the place to go for beautiful beaches. However, the entire island stank of sulfur, thanks to the ongoing geologic activity, and the beaches were dirty and crowded. It would have been much better to spend the day relaxing on the beaches around Taormina. We drove back to our hotel and ate a delicious dinner at the Hotel Villa Ducale Ristorante, which, perched high above Taormina, offers great views of the town.

The next morning, we woke up and hiked to Chiesa Madonna della Rocca, a church high above Taormina that was originally carved from a cave. its origins are still obvious, as a large natural rock formation composes much of the ceiling. The church also has stunning views of Taormina and the Ionian sea. In the early afternoon, we drove to Catania to catch a flight to Rome.

We landed in Rome in the early evening, checked into our hotel, and caught a cab to the city center, where we ate dinner. Then we sprinted through some of Rome’s top sights: the Spanish Steps, the Trevi Fountain, the Forum of Caesar, and the Colosseum. We returned to the hotel and went to bed, ready to catch an early flight home in the morning.