70km (43 miles) S of Florence; 232km (144 miles) N of Rome

Siena is a medieval city of brick. Viewed from the summit of the Palazzo Pubblico's tower, its sea of roof tiles blends into a landscape of steep, twisting stone alleys. This cityscape hides dozens of Gothic palaces and pastry shops galore, unseen neighborhood rivalries, and painted altarpieces of unsurpassed beauty.

Siena is proud of its past. It trumpets the she-wolf as its emblem, a holdover from its days as Saena Julia, the Roman colony founded by Augustus about 2,000 years ago (though the official Sienese myth has the town founded by the sons of Remus, younger brother of Rome's legendary forefather). Siena still parcels out the rhythms of life, its rites of passage and communal responsibilities, to the 17 contrade (neighborhood wards) formed in the 14th century. Compared with its old medieval rival, Siena is as inscrutable in its culture, decorous in its art, and festive in its life attitude as Florence is forthright, precise, and serious on all counts. Where Florence produced hard-nosed mystics such as Savonarola, Siena gave forth saintly scholars like St. Catherine (1347-80) and St. Bernardino (1380-1444).

Its bankers, textile magnates, and wool traders put 12th-century Siena in competition with Florence, and the two cities kept at each other's throats for more than 400 years. When Florence went Guelph, Siena turned Ghibelline and thrashed Florence at the 1260 Battle of Montaperti. Unfortunately for Siena, the battle was fought in alliance with ousted Florentine Ghibellines, who refused to allow the armies to press the advantage and level Florence. Within 10 years, Charles of Anjou had crushed the Sienese Ghibellines.

With Siena now Guelph again, Sienese merchants established in 1270 the Council of Nine, an oligarchy that ruled over Siena's greatest republican era, when civic projects, the middle-class economy, palace building, and artistic prowess reached their greatest heights. Artists like Duccio, Simone Martini, and the Lorenzetti brothers invented a distinctive Sienese art style, a highly developed Gothicism that was an artistic foil to the emerging Florentine Renaissance.

Then, in 1348, the Black Death hit the city, killing perhaps three-quarters of the population, decimating the social fabric, and devastating the economy. The Council of Nine soldiered on, but Charles IV attacked Siena from 1355 to 1369, and although Siena again trounced Florence in 1526, the Spanish took control in 1530 and later handed Siena over to Ducal Florence.

To subdue these pesky Sienese once and for all, Cosimo I sent the brutal marquis of Marignano, who besieged the city for a year and a half, destroying its fields and burning its buildings. By the time he stormed the city in 1555, the marquis had done more damage than even the Black Death -- only 8,000 out of a population of 40,000 had survived -- and the burned and broken city and countryside bore an uncanny resemblance to the Effects of Bad Government, half of Ambrogio Lorenzetti's fresco in Siena's Palazzo Pubblico. Some 2,000 fiercely independent Sienese escaped to Montalcino, where they kept the Sienese Republic alive, in name at least, for another 4 years. Then Montalcino, too, was engulfed by Florence. Siena became, on paper and in fact, merely another part of Grand Ducal Tuscany. Since the plague of the 14th century, Siena was so busy defending its liberty it had little time or energy to develop as a city. As a result, it offers your best chance in Tuscany to slip into the rhythms and atmosphere of the Middle Ages.