Palazzo Vecchio

Florence's town hall has been in continuous operation since 1299, making it one of the oldest functioning government buildings in the world. When the Florentines decided to build it, they had a peculiar requirement: the building could not sit on land once owned by the defeated Ghibelline faction. This is why the palazzo is slightly off-center from the piazza — the architect Arnolfo di Cambio had to work around property lines of political enemies.

The 94-meter Arnolfo Tower that juts from the roofline was both a watchtower and a power statement, visible from every approach to the city. In its cells, Cosimo de' Medici was briefly imprisoned before his exile in 1433, and Savonarola was tortured here before his execution. Niccolò Machiavelli worked in the building as Second Chancellor from 1498 to 1512, in a modest office that still exists — the man who wrote The Prince spent his days handling Florence's military correspondence from this very room.

Inside, the Salone dei Cinquecento is a jaw-dropper — a 54-meter-long hall commissioned by Savonarola to hold his 500-member council, later redecorated by Vasari with enormous battle paintings. Behind one of those paintings, art historians believe, may lurk a lost Leonardo da Vinci mural — the Battle of Anghiari. Vasari left a cryptic clue painted on a flag in his own work: "Cerca trova" — "Seek and you shall find."

The entire building sits on top of a first-century Roman theater, whose stone seating you can walk through in the underground excavations. Seven centuries of Florentine power, built on Roman ruins, still running the city today.