164km (102 miles) SE of Florence; 176km (109 miles) N of Rome

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. In addition to one the finest art galleries in Italy, there are several important churches and smaller museums to see, but it's this combination of shops, bars and sights -- the juxtaposition of medieval and contemporary Umbria -- that makes the city so appealing. Perugia is also a respected university town, whose student population ensures a lively cultural calendar.

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 the Goths, but it became subject to the Lombard Duchy of Spoleto in the later 6th century.

By the Middle Ages, Perugia was a thriving trade center and had begun exhibiting the bellicose tendencies, vicious temper, violent infighting, and penchant for poisons that would earn it such a sunny reputation among contemporary chroniclers. The Oddi and Baglioni were just two of the noble families who waged secret vendettas and vied with the middle-class burghers for absolute power. Burgher Biordo Michelotti, egged on by the pope, managed to seize power in 1393 by murdering a few rivals from the Baglioni family. Five years later, his despotic rule ended with a knife in the back. A period of relative calm came in 1416 with the stewardship of Braccio Fortebraccio ("Arm Strongarm"), under whose wise and stable rule the city's small empire expanded over the Marches region. In the end, he was done in by a fellow Perugian while he was besieging L'Aquila in 1424. And then there were the Baglioni.

When their rivals, the Oddi, were run out of town in 1488, the field was more or less clear for the Baglioni to reign in all their horrible glory. The family turned assassination, treachery, and incest into gruesome art forms. When not poisoning their outside rivals, they killed siblings on their wedding nights, kept pet lions, tore human hearts out of chests for lunch, and married their sisters. In a conspiracy so tangled it's almost comic in its ghastliness, the bulk of the family massacred one another on a single day in August 1500.

The last of the surviving Baglioni, Rodolfo, tried to assassinate a papal legate in response to his uncle's murder at the hands of the pontiff. All that did was anger Pope Paul III, who upped the salt tax a year after promising otherwise. The rebellion Paul was trying to provoke ensued, giving the pope the excuse he needed to subdue the city. Papal forces quickly quashed the city's defenses and leveled the Baglionis' old neighborhood. After riding triumphantly into town, the pope had all Perugia's nuns line up to kiss his feet, an experience he reported left him "very greatly edified."

The enormous Rocca Paolina fortress he built to keep an eye on the city quelled most rebellious grumblings for a few hundred years, during which time the Perugini slowly mellowed. Since Italian unification in 1860, Perugia has thrown its energies into becoming the most cosmopolitan medieval city in the world. 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 famous Baci chocolates, and the city stages an urbane and stylish passeggiata stroll every evening and one of Europe's most celebrated jazz festivals every summer.