The origins of Castellina in Chianti go back until the 7th century B.C. A whole series of Etruscan villages and hamlets once existed along a major route following the crest that passes through Castellina and provided a link between the great cities of Vulci, Vetulonia and Roselle – and the markets of the north, particularly Spina, the most important trading harbour on the Adriatic and the gateway to the East.
Many important archaeological finds have come to light in Castellina, particularly the imposing burial vault of Mt. Calvario, which measures about 53 metres across, just outside the town on the road to Florence. The tomb contains four burial vaults arranged in a cross aligned with the four cardinal points. The hill takes its name from a little chapel that once stood on the summit, the last station of the Way of the Cross.
At Poggino, to the east of the village of Fonterutoli, along the old road towards Siena, archaeologists have unearthed a small necropolis containing five tombs, four with burial chambers and one small rectangular chamber shaped like a chest. Artifacts found among the burial objects show that rich families of noble birth lived in this region throughout the 6th century B.C., the Etruscan period of greatest splendour which, according to Diogenes of Halicarnassus, “has no peer”. Castellina continued as a settlement in Roman times up until the 1st century B.C. but traces of sudden destruction followed by a fire indicate that the town came to a tragic end.