It was an Etruscan and Roman town and in the year 814 the Emperor Ludovico il Pio put it under the control of S.Antimo Abbey.

In the 12cent. Montalcino became a free city allied to Siena,but nevertheless rival to it. The massive fortress was builted after the battle in Montaperti, in the year 1361, when Montalcino surrendered.

The fortress "La Rocca",hold out against Pope Clemente VII soldiers' attacks and also against Imperial army's attacks, when even Siena surrendered.

Montalcino ended up to submit to Granduca Cosimo I de' Medici,starting to be influenced by Medicean world.

Today it is famous mostly for its wine "Brunello di Montalcino", very well known all over the world, thanks to grape-grower Ferruccio Biondi Santi, who decided to produce wine just with Sangiovese grapes and getting the wine aged in oak and chestnut barrels for at least 5 years.