The very high site of the town provides views over the Asso, Ombrone and Arbia valleys of Tuscany, dotted with olive orchards, vineyards, fields and villages.

During the late Middle Ages it was an independent commune with considerable importance owing to its location on the old Via Francigena, the main road between France and Rome, but increasingly Montalcino came under the sway of the larger and more aggressive city of Siena.

Once Siena had been conquered by Florence under the rule of the Medici family in 1555, Montalcino held out for almost four years, but ultimately fell to the Florentines, under whose control it remained until the Grand Duchy of Tuscany was amalgamated into a united Italy in 1861.

The fortress, built in 1361 atop the highest point of the town, was designed with a pentagonal layout by the Sienese architects Mino Foresi and Domenico di Feo.

Though the town itself was eventually conquered, the fortress itself never submitted, an admirable feat, considering the size of the Sienese and Florentine forces that besieged Montalcino at varying intervals.

The Duomo (cathedral), dedicated to San Salvatore, was built originally in the 14th Century, but now has a 19th-century Neoclassical façade designed by the Sienese architect Agostino Fantasici.

Montalcino is divided, like most medieval Tuscan cities, into quarters called contrade, Borghetto, Travaglio, Pianello and Ruga, each with their own colors, songs and separate drum rhythms to distinguish them.

Twice a year they meet together in a breath taking archery contest under the walls of the Fortezza, conducted in Medieval dress, with lords and ladies of each contrada who accompany the proceedings.

Associated with the Fête de la Musique, created in 1981 in Paris to celebrate music and musicians, the Festa was incorporated into the Italian Minister of Culture's agenda in 1994, and has since spread across Italy.