Siena

Siena is the city Florence might have become if the Black Death hadn't gotten there first. In 1348 the plague took more than half the population, the building stopped, and the Gothic masterpiece they were raising simply stayed put. What's left is the most complete medieval city in Italy — brick streets the color of the surrounding hills, a piazza shaped like a scallop shell, and seventeen neighborhoods that still run a bareback horse race twice a summer as if nothing has ever mattered more.

It also happens to sit dead center in the best part of Tuscany, which makes it a far smarter base than its famous rival. Wine country, lunar clay hills, and a dozen hill towns are all within an hour. Come for a day and you'll see why people stay for three: when the buses leave at five and the brick goes gold, Siena hands itself back to the people who live in it — and that's the city worth knowing.