Perugia,
Perugia is a capital city in a medieval hill town's clothing -- a town of Gothic palaces and jazz cafes, where ancient alleys of stone drop precipitously off a 19th-century shopping promenade. It produced and trained some of Umbria's finest artists, including Gentile da Fabriano and Perugino (born Pietro Vannucci in nearby Città della Pieve), from whose workshop emerged Pinturicchio, Lo Spagna, and Raphael. It's a respected university city whose student population ensures a lively cultural calendar. After a long and bloody history, Perugia seems to have settled well into its role as capital of Umbria.
Perugia was one of the 12 cities of the Etruscan confederation, and though it submitted to general Roman authority in 310 B.C., it remained a fractious place, always allying itself with a different Roman faction. It chose the losing side in Octavian's war with Marc Antony, and when the future emperor defeated Marc Antony's brother here in 40 B.C., a panicked Perugian noble set fire to his house in a suicide attempt. The flames spread quickly, and most of Perugia burned to the ground. Soon after, Octavian, now Emperor Augustus, rebuilt the city as Augusta Perusia. Throughout the Dark Ages, Perugia held its own against the likes of Totila the Goth, but it became subject to the Lombard Duchy of Spoleto in the later 6th century.
It's home to one of Italy's largest state universities as well as the Università per Stranieri, the country's most prestigious school teaching Italian language and culture to foreigners. Local industry's biggest name is Perugina, purveyor of Italy's finest chocolates, and the city stages an urbane and stylish passeggiata stroll every evening and one of Europe's most celebrated jazz festivals every summer.