A legend say in 781, Charles the Great, turning back from Rome and after crossing Mount Amiata where Black dead raged, decided to built a church to thank God for escaped danger. In that Place now, there is the Abbey of Sant’Antimo.
There are documents about the donation from Ludovic the Pius in 814 of the territory of Montalcino to the Abbey. In this period, some Etruscan who lives in the coast, to escape from incursions by Saracens, leaved their town and they went to inland country and they founded the town in the 10th century. Montalcino live with prosperity for the production of earthenware, wool, skins, iron and trading.
In 1110, Montalcino was fortyfing by Siena, for his strategic position on Route Francigena (that links Rome with France) and so this town became pratically impenetrable. In this time, Montalcino was always rich for his trading and his handycraft. So to be near Siena (that is so much rich ) created a particular relations between these towns.War and peace alterned for many years, since 1261, when Siena in Montaperti’s battle defeated the enemies Montalcino and Florence and so Montalcino going back under the administration of Siena. These years was in true peace and so in 1361 Montalcino obtained the citizenship of Siena.
In 1555, a German-Spanish army allied with Florence defated Siena, Montalcino give asylum to the refugees and for 4 years, here lived the Last Republic: following the treaty of Chateau-Cambrèsis between France and Spain, Montalcino, in 31th of July of 1559, gived his keys to Don Giovanni Guevara and became part of the Grand Duchy of Tuscany