Castellina in Chianti: The History of a Fortified Town

The first historical documents about Castellina -though the area was certainly inhabited ever since ancient times - date back to the Middle Ages. In the eleventh century, Castellina was mentioned as a settlement under the control of the nearby castle of Trebbio (corresponding to the present day village of Trebbia in the borough of Radda in Chianti) owned by the Conti Guidi who built the first fortifications. At that time, the area was known as "Castellina de‘Trebbiesi". In 1193, following an agreement signed by the masters of Trebbio, the castle was garrisoned by the Florentines.

In the mid-thirteenth century, Castellina joined the Chianti League, becoming the capital of one of the three areas (the other two capitals were Radda and Gaiole) into which the League was divided; the area, in fact, was called ‚"Terzo di Castellina". As is known, during the whole of the Middle Ages, Chianti was tormented by clashes and battles between Florence and Siena.

Dominating the ridgeway connecting the two cities, the town was one of the most southerly Florentine strongholds and consequently a very important strategic
element. In 1397, the castle was destroyed by the troops of the Duke of Milan, an ally of the Sienese. A few years later, in 1400, the Republic of Florence decided to strengthen the defences by building a thicker and solider ring of walls, featuring an irregular hexagonal shape, numerous square towers, two gates, one facing Siena and the other facing Florence, and crowned at the highest point of the town by a massive battlemented keep with escarpment walls. Long sections of the walls
and the towers encircling the town still remain, though they have often been incorporated in houses, and the two gates no longer exist: the one facing Florence was destroyed during the Second World War (what we see today is a recent opening in the walls).

The keep, comprising two square buildings, with its high walls, is in perfect condition, thanks to painstaking restoration work carried out at the beginning of the twentieth century. Today it is the town hall. This powerful fortification was baptised by fire in 1452 when it resisted the siege of the Duke of Calabria for 44 days. It seems that at that time Castellina had been further strengthened by the famous Medicean architect, Giuliano da Sangallo. In spite of this, in 1478, the castle surrendered to the army of Aragon and, just like other nearby ones, it was sacked and half destroyed. In 1483, Castellina finally returned to Florence.

In 1774, the Chianti League was abolished but the land of the new "Community of Castellina", established by the reforms brought about by Grand Duke Pietro Leopoldo, almost perfectly coincides with the ancient "terzo" of the League, as does the current borough in the province of Siena A short tragic event of war involved Castellina in 1944; the retreating German troops, favoured by the rough terrain, set up a defensive line right in the town which caused dozens of deaths among the civilian population and much destruction.


(Portions of this article first appeared in "Toscana & Chianti News")
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