With its narrow streets and steep alleys, a Gothic Duomo, a bounty of early Renaissance art, and the glorious Palazzo Pubblico overlooking its magnificent Campo, Siena is often described as Italy's best-preserved medieval city. It is also remarkably modern: many shops sell clothes by up-and-coming designers. Make a point of catching the passeggiata (evening stroll), when locals throng the Via di Città, Banchi di Sopra, and Banchi di Sotto, the city's three main streets.

Sienese mythology holds that the city shares common ancestry with Rome: the legendary founder, Senius, was said to be the son of Remus, the twin brother of Rome's founder, Romulus. The city emblem—a she-wolf and suckling twin boys—promulgates the claim. Archaeological evidence suggests there were prehistoric as well as Etruscan settlements here, which undoubtedly made way for Saena Julia, the Roman town established by Augustus in the 1st century BC.

Siena rose to prominence as an essential stop on that most important of medieval roads, the Via Francigena (or Via Romea), prospering from the yearly flow of thousands of Christian pilgrims coming south to Rome from northern Europe. Siena developed a banking system—one of Europe's oldest banks, the Monte dei Paschi, is still very much in business—and dominated the wool trade, thereby establishing itself as a rival to Florence. The two towns became regional powers and bitter enemies, each taking a different side in the struggle that divided the peninsula between the Guelphs (loyal to the Pope) and Ghibellines (loyal to the Holy Roman Emperor). Siena aligned itself with the latter.

Victory over Florence in 1260 at Montaperti marked the beginning of Siena's golden age. Even though Florentines avenged the loss 29 years later, Siena continued to prosper. During the following decades Siena erected its greatest buildings (including the Duomo); established a model city government presided over by the Council of Nine; and became a great art, textile, and trade center. All of these achievements came together in the decoration of the Sala della Pace in Palazzo Pubblico. It makes you wonder what greatness the city might have gone on to achieve had its fortunes been different, but in 1348 a plague decimated the population, brought an end to the Council of Nine, and left Siena economically vulnerable. Siena succumbed to Florentine rule in the mid-16th century, when a yearlong siege virtually eliminated the local population. Ironically, it was precisely this decline that, along with Sienese pride, prevented further development, to which we owe the city's marvelous medieval condition today.

But although much looks as it did in the early 14th century, Siena is no museum. Walk through the streets and you can see that the medieval contrade, 17 neighborhoods into which the city has been historically divided, are a vibrant part of modern life. You may see symbols of the contrada—Tartuca (turtle), Oca (goose), Istrice (porcupine), Torre (tower)—emblazoned on banners and engraved on building walls. The Sienese still strongly identify themselves by the contrada where they were born and raised; loyalty and rivalry run deep. At no time is this more visible than during the centuries-old Palio, a twice-yearly horse race held in the Piazza del Campo, but you need not visit then to come to know the rich culture of Siena.

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