about 108 km, 1 hours + 10 min

This city is located roughly at the center of Sicily, towering above the surrounding countryside. It has earned the nicknames "belvedere" (panoramic viewpoint) and "ombelico" (navel) of Sicily. Enna is the highest Italian province capital.

Archaeological findings dating from the 14th century BC have proved the human presence in the area since Neolithic times. A settlement from before the 11th century BC, assigned by some to the Sicani, has been identified at the top of the hill; later it was a center of theSiculi. In historical times it became renowned in Sicily and Italy for the cult of the goddessDemeter (the Roman Ceres), whose grove in the neighborhood was known as the umbilicus Siciliae ("The navel of Sicily"); the origin of the toponym Hennaremains obscure.

After the fall of the Western Roman Empire, it continued to flourish throughout the Middle Ages as an important Byzantine stronghold. In 859, in the course of the Islamic conquest of Sicily, after several attempts and a long siege, the town was taken by Muslim troops who had to sneak in one by one through a sewer to breach the town's hardy defenses. The name for the city, 'Qas'r Ianni' (Fort of John), was a combination of "qas'r" (a corruption of the Latin "castrum", fort), and "Ianni", a corruption of "Henna". The name in the native dialect of Sicily remained Castro Janni (Castrogiovanni) until the renaming by order of Benito Mussolini in 1927. The Normans captured her in 1087. Frederick II, Holy Roman Emperor and King of Sicily, established a summer residence here.

Enna had a prominent role in the Sicilian Vespers that lead to the Aragonese conquest of Sicily, and thenceforth enjoyed a short communal autonomy. King Frederick III of Sicily favored it and embellished the city; it however suffered a period of decay under the Spanish domination. It was restored as provincial capital in the 1920s. It has become a university city in 2002.