In many ways Siena hasn’t changed much in 800 years. And that’s a good thing. The town’s gorgeous 13th-century main square, the Piazza del Campo, is still the city’s symbolic and physical heart. The twice-a-summer bareback horse race, Il Palio, is still the most anticipated event, and the contrade, or neighborhood associations, still inspire a loyalty as deep as they did in medieval times. At the same time the ancient university here continues to deliver important research while imbuing the town with a youthful spirit. Florence, Siena’s biggest rival to the north, may have won the battle in terms of historical significance and blockbuster art over the centuries, but Siena is decidedly less touristy and more livable. In the past few years, new boutiques and wine bars (not to mention updated restaurants) have been sprinkled in among some newly restored treasures.

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