42km (26 miles) S of Siena; 112km (70 miles) S of Florence; 190km (118 miles) NW of Rome

Montalcino presents a mighty image on the approach from the valley -- a walled town set high on a hill punctuated with the spires of medieval buildings and a glowering fortress at one end. Up close, it becomes a smaller, meeker place, but the precipitous medieval alleyways and stone buildings make it a day-trip delight, and the views of the valleys from which you ascended are magnificent from this height.

Paleolithic tribes and the Etruscans set up camp here, but it wasn't until the Roman era that a permanent settlement formed. By the Middle Ages, Montalcino was a bustling town and a defensive center for the surrounding farming community. Although it divided itself into four minuscule neighborhood contrade (neighborhoods) after the Sienese model, Montalcino was initially allied to Florence and at odds with its northerly neighbor Siena. After several skirmishes, though, the Sienese took over Montalcino in the 13th century. By 1462, the town had grown large enough to be declared a city, and in 1555 its now-cozy relations with Siena led it to harbor the 700 Sienese families who refused to submit to the Medici when Florence defeated Siena. The exiles set up the defiant "Republic of Siena at Montalcino," which lasted 4 years until the Medici grand dukes finally laid their hands on both the Sienese and Montalcino through treaty. Montalcino's loyalty is honored to this day -- their standard-bearer rides in pride of place at the front of Siena's annual pre-Palio parade.

Montalcino's Medici-induced slide into obscurity began to turn around in the 1960s, when the world discovered that the sangiovese grosso grapes -- known as "Brunello" to the locals, who had been quietly experimenting with them for about a century -- made one of the finest red wines in the world. Today, with an annual production of more than 3.5 million bottles of Brunello di Montalcino -- and 3 million of its lighter-weight cousin Rosso di Montalcino -- Montalcino has become a rather well-to-do town, also known for its white dessert wine called Moscadello and its fine honey.