Its first inhabitants were the Etruscans, their presence has been proved by many archaeological finds in the hills around Castellina, where a sepulchral tumulus of Montecalvario has been found, dating back to the half of VII and the begins of the VIII century b.C. Etruscans were the first to exploit the territory, they planted vines and cultivated olives.
In that period little villages developed and habitations were based on farm; later with the arrive of Romans, during the imperial age, it becomes the typical way of life, symbol of a large number of countrymen who cultivated their fields to maintain themselves.
After the fall of the Roman Empire, the Longobards came down to Italy and settled in Chianti, where they remained also after the occupation of Francs. The Vicchimaggio’s castle is called “Vico of Longobards” in some documents of the X century.
In that period the population in the small villages and in the rural companies grew, they were composed by few houses placed around a religious building.
At the end of the high Middle Ages the first castles appeared and they represented between the X and XII century the nucleus on which the development of all area was based.
After a first phase when a lot of castles were built, there was a period when they were used like check point of the boundary line that separated the municipal Florentine and Sienese territories, for a long time in contrast, because they were of two different factions Guelph and Ghibelline.
In the early years of 1200 , in Fonterutoli , two deals of peace were signed, they recognized to Florence the greater part of the Chianti’s territory, which was organized in the “Chianti-League” and they used a black rooster as an emblem.
On the 4th september 1260 in the Montaperti battle the Guelph army of Florence was beaten by the Sienese Ghibelline army. The winners established a temporary hegemony on the region, even if for a short time.
In 1266 with the Benevento’s battle and the rise of the angioina family on the throne of Naples, the Ghibelline domination finished. This caused a deep change in the relation in Tuscany, sanctioned from the defeat suffered by the Sienesi in Colle Val d’Elsa in 1269.
Because of internal fights and the rise of the Florentine lordship between the XIV and XV century, Siena was conquered in 1555, after a long siege of Cosimo I de’ Medici after the victory of Marciano of the Chiana. This date marks the beginning of a series of historical events happened in the following centuries, events of fortune and misfortune of noble families of Chianti,
who had to swear fidelity to the Florentine lily or to the Sienese “balzana” until the annexation of their lands to the Grand Duchy of Tuscany.