-- Sicily's Prettiest Towns -- 10 Must-Explore Cities

by Christopher Atwood


Picking the most beautiful town in Sicily is a bit like asking an Italian what’s their favorite pasta. Endless answers abound but, really, it comes down to a question of  taste.  Do you prefer the gold-mosaic grandeur of Monreale or the seaside charms of Cefalù? Do you want to eye Mt. Etna from inside Taormina’s Greco-Roman theater or to make chocolate with a nonna in Modica?

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There is no one Sicily. There are countless Sicilies to discover. So, what are Sicily’s prettiest towns? Read below to find the Top 10 Sicilian towns to explore during your Italy travels:


Standing high above the west coast of Sicily (2,400 feet above sea level) and at times shrouded in a cloud, Erice is a picturesque medieval town—where travelers can walk back in time, all while drinking in sweeping views of Sicily’s stunning seascape.  What are the best things to see in Erice, Sicily? In existence since ancient times, Erice vaunts two castles (Castello di Pepoli and the Norman Castle), 60 churches and a cluster of cobbled stone streets.


On clear days, you can see all the way out to the Egadi Islands—which surge from the sea west of Trapani.  Glancing to the east, you can eye the sapphire-blue Gulf of Castellammare. In Sicily, Erice is famed for its feast of local sweets—including fruit-shaped marzipan, honey-spiked mustazzoli biscotti, and the custard-filled genovesi cookies. You can savor these traditional Sicilian desserts at the family-run Pasticceria Maria Grammatico, which has been selling sweets since 1955!


Ragusa is one of southern Sicily’s most postcard-perfect villages. Boasting Baroque palaces and an easy-to-navigate grid of streets, Ragusa makes for the perfect place to wander and explore on foot. The Old Town here is called Ragusa Ibla and is perched on a hilltop overlooking the surrounding valleys. Having been rebuilt after a massive earthquake in 1693, Ragusa’s architecture reflects the elaborate Baroque style – brimming with florid details, sculpted facades and ornamented columns.


Interestingly, Ragusa is a city split in two by a deep ravine called the Valle dei PontiRagusa Superiore is the modern portion, seated on the top of the hill here.  Travelers can walk with a local guide from Ragusa Superiore to the older Ragusa Ibla—passing the 15th-century Santa Maria delle Scale church and vistas of the ravine’s plant-draped cliffs. To arrive in Ragus Ibla, travelers clamber down the Salita del Commendatore – a stone stairway, framed by historic palazzi and archways, connecting the upper and lower towns.   


Perhaps Sicily’s most famous town among visitors, Taormina has been attracting foreign travelers since the Grand Tour.  Taormina’s history is Sicily incarnate – having been conquered and inhabited by the Greeks, Romans, Byzantines, Arabs, Germans, Normans and Spanish over the centuries.  Clinging to a sea cliff that juts out over the glittering Ionian Sea, Taormina still occupies the site were its ancient counterpart once thrived.  The Old Town stands at 820 feet above sea level, offering views of the cloud-hugged Mt. Etna in the distance and the 10th-century Saracen Castle (Castello Saraceno) high above.  You can reach the castle on foot by a staircase at the base of the Madonna della Rocca Church (built in 1640).


So, what are the best things to see and do in Taormina, Sicily? Centuries-old history is on full display on Taormina’s stone streets.  A must-see in Taormina is the Greco-Roman amphitheater, which is also called the Greek Theater.  First built by Greek settlers in the 3rd-century BC, the theater was later expanded by the Romans—who added still-visible columns and porticoes.  Scenically posed above the sea, the theater looks out over snow-capped Mt. Etna and the Italian mainland.  For a slightly more modern view, head to Taormina’s Piazza IX Aprile – crowned in iconic black and pink-white stone tiles. This sublime square vaunts sea views, the Gothic St. Augustine Church and the 17th-century Church of St. Joseph.  Beach lovers might also spend a day in the lower town, idling away on the sublime shores of Isola Bella.


Siracusa – often called Syracuse in English – is marvel of Mediterranean civilization. First founded in 734BC by Greek colonists, Siracusa once rivaled Athens as a center of learning, trade and power. Later, Siracusa continued to thrive a hub of Roman, Byzantine and Jewish culture in the Mediterranean.  To this day, a vast archeological site lies on the outskirts of town – including crumbling temples, stone theaters, and Castello Euralio (400BC). Beyond ruins, though, what sights are there to see on a trip to Siracusa, Sicily?


Siracusa’s old town, curiously, is located on Ortigia island—connected to the mainland by three bridges.  Ortigia’s tight-knit lanes are ideal for lazy strolling—as you explore medieval alleyways and Baroque palazzi kissed by salt air from the port.  Piazza Duomo here boasts the impressive Cathedral of Siracusa—constructed atop the old Temple of Athena.  Around the perimeter of the island, you’ll find the fortified walls of Castello Maniace—a stronghold built by Emperor Frederick II in 1232.  Seafood lovers in Ortigia should consider lunch at Tavernetta da Piero; here, you can savor Siracusan specialties such as fish carpaccio, mussel stew and pasta with swordfish. 


Sicily’s less touristy southeast boasts a bounty of Baroque beauties – with towns vaunting wine-yellow palaces and hand-sculpted facades that soak in the sun.  Separated from the rest of Sicily by craggy mountains and deep gorges, this quadrant of the Sicilian isle was once a muddle of meandering medieval alleys.  A powerful earthquake in 1693 flattened most of the older towns – allowing for a more modern style -- including straightened boulevards and lavish ornamentation -- to arise here.  Towns such as Noto, Ragusa, Scicli, Catania, Caltarigione and Modica embody this Baroque style—so much so that the UNESCO declared the Val di Noto’s Baroque towns a World Heritage site in 2002.


Located just a twenty minutes’ ride from the larger Ragusa, Modica’s charms merit a leisurely day trip or overnight stay.  Spread out over numerous stone spurs, Modica’s old walled town stands high above the Baroque city below—linked together by 250 scenic stone steps. Along Corso Umberto, Modica’s main avenue, you can still spot gaggles of older man gathered around a game of cards.  What else is there to do in Modica, Sicily? Well, during the Baroque period, this part of Sicily was under Spanish rule – and, thus, had more trade with the New World. As a result, that most exotic of American ingredients ­– chocolate – was introduced early to Sicily. Modica’s cooks quickly proved themselves master chocolatiers, transmuting sugar and cacao into succulent sweets. To this day, you can enjoy a hands-on chocolate-making class (and tasting) in Modica’s family-run chocolate shops.


To Sicilians, Caltagirone means one thing—ceramic tiles. Whether you’re strolling past the town’s Baroque palazzi or descending the 142 steps of the Scalinata di Santa Maria, Caltagirone is literally covered in glazed tiles – featuring swirling colors, crafted by hand.  The Scalinata di Santa Maria is the most famous example of Caltagirone’s artisan ceramics. Each step’s vertical face is adorned with brilliantly-hued tiles. You can walk this scenic staircase to get from the old town to the more modern area down below. With our local guides, you might also go behind-the-scenes with a master ceramic artist in Caltagirone – observing how humble clay morphs into elegant earthenware. Caltagirone is just 40 minutes from Catania—home to one of Sicily’s two main airports.     



Most visitors to Sicily are seduced by the island’s scenic seaside towns, skipping the equally stunning inlands. While it’s undeniable that coastal cities like Palermo and Cefalù are glittering gems, the most postcard-perfect villages on Sicily are actually found further in – perched atop the island’s volcanic bluffs or rugged hills.  Sant’Angelo Muxaro -- located not far from Agrigento’s famous Valley of the Temples (Valle dei Templi) -- is one such village.  What is there to see and do in Sant’Angelo Muxaro?


Well, village life in Sicily revolves around two things – famiglia (family) and tradizione (tradition).  Sant’Angelo Muxaro embodies both, boasting a family-run bakery where you can learn to make the typical pani cunzato – crowned in ripe tomatoes, extra virgin olive oil, garden oregano and local cheese. Near the same hilltop town, you can visit with a family of sheep herders – learning how they produce pistachio-studded pecorino from the milk of free-range animals.   


Located on the north side of the island, Cefalù is one of Sicily’s more spectacular seaside towns and beach destinations.  The town itself is dominated by a massive rocca (stone) that stands 270 meters in height.  Atop the bluff, you’ll find the rocky remains of the Temple of Diana—dating to the 5th century BC.  Down below, whitewashed homes and building made from golden-beige stones frame the quiet, sandy bay. In the harbor, traditional fishermen’s boats – painted bright colors – bob and sway in the waves. History buffs should explore the Duomo di Cefalù (cathedral), which was erected by Norman conquerers in 1131 AD.  In the evening, you can watch the sun dip under the sea here from a bench along the town’s scenic lungomare (waterfront).



Enna is the highest provincial capital in all of Italy – towering above the surrounding landscape at 3,054 feet above sea level.  This marvel of masterful engineering has been inhabited by humans since the Neolithic times — framed by steep cliffs, green valleys and blue-green seas off in the distance. Enna’s duomo (cathedral), built in 1307, boasts a massive staircase, multicolored marble inlays and hand-shaped wooden roof.


Summertime visitors might stumble across the procession of Madonna della Visitazione on July 2nd here —when a statue of the city’s patron saint is hoisted by the faithful through town.  But perhaps the biggest draw here is the majestic Castello di Lombardia, which is a fortified castle in use since the 1,000BC!  Before you leave Enna, be sure to nibble on the local sweet of choice -- buccellati biscotti filled with figs or almonds.


Not far from Palermo, you’ll find the Arab-Norman marvel called Monreale. The town’s cathedral, constructed between 1170 and 1189, has been declared a Unesco World Heritage Site — vaunting impeccably-preserved Norman architecture and inlaid mosaics containing over 2,200 kg of pure gold. The church blends Islamic, Byzantine and Romanesque styles—a visual reminder that Jews, Muslims, French, Lombards and Greeks once coexisted here.   



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