Dating from the 7th century BC Castellina in Chianti’s origins are comparable with many of Tuscany’s ancient towns, as does Castellina’s Etruscan links.
At one time a major trade route following the ridge that passes through Castellina provided a link between the great cities of maritime Etruria – Vulci, Vetulonia and Roselle – and the markets of the north, especially Spina, the most important trading harbour on the Adriatic and at that time the gateway to the East.

Named after the Biblical Calvary Mt Calvario has a 53m wide burial vault whilst at Poggino close to Fonterutoli a small necropolis containing five tombs have been found.
Castellina lay on the border of the Etruscan territories of Volterra, Chiusi and Fiesole all of which were enemies and this ancient border is reflected today in the division of the Castellina region between the dioceses of Siena and Fiesole.

Castellina’s military strength was largely due to its strategic location, enabling control of the surrounding roads and Elsa valley. Evidence of the town’s importance is its renowned and imposing castle and the fact that the town was surrounded by impregnable walls and towers, and only two entrance gates: both gates have since been destroyed, but most of the walls still stand today.

Attractions today include the 15th century Rocca Comunale, the 16th century Church of San Salvatore, the Via delle Volte, Via Ferruccio and nearby town of Fonterutoli.

Castellina is of course a centre of the production of the renowned Chianti Classico wine and no traveller should miss a chance to visit a local winery or two whilst in the area.