WHAT TO KNOW

Known for their penchant for hilltops, the Etruscans likely first settled Montalcino. However, the first inhabitants were not recorded until the ninth century. In the decades to come, the medieval city grewand prospered enough to spark the interest of Siena and Firenze, the major Tuscan players between 1200s-1500s. The two cities battled for centuries over Montalcino. Scrappy and strong, Montalcino held its own for a few years, using the same rocky fortress that the other Tuscan cities built to fight each other to defend itself. After a while, though, Montalcino fell under Florentine rule until Italy’s unification in the 19th century.

WHERE TO GO

Start your tour at the top of the town, where the Rocca – the ancient fortress – still stands strong, ready to defend the town against invaders. Built in 13th century, the fortress affords spectacular views and makes a charming setting for festivals, concerts, and other events. From there, proceed downhill to Musei Riuniti, a museum with beautiful art and architectural wonders. Continue to stroll around the labyrinth of stone streets, cafes, restaurants, and wine bars. (Nota bene: stroll is the word, as the steep hills can wind even the fittest walkers.) As you adventure, keep an eye out for the different symbols of the ancient contrade, or the small neighborhoods of the town, which still practice their own colors, songs, cultures. Twice a year, they hold magnificent archery contests, authentic down to the medieval dress and feasting.

WHAT TO TASTE

The olive trees and vineyards that overtake Montalcino’s lower slopes belie the town’s delicious tradition of winemaking and olive oil production. Do not leave Montalcino without tasting the town's famous wines and extra virgin olive oils. The best known of the wines is Brunello di Montalcino, which is DOCG-protected and made with the local Sangiovese varietal. After centuries of practice, the vintners are masters at every type, be they Super Tuscan blends or rosy rosés.