The town of Castellina in Chianti still preserves the characteristic features of its medieval buildings both in the medieval houses and streets paved in stone and in its ancient fortifications. The village is surrounded by large stretches of its ancient city walls of irregular hexagonal shape, built in the Fifteenth century by the Florentine Republic. It is still interspersed with many square towers and is crowned by a massive rectangular tower representing the higher and of a fortified castle. Of great interest is the tower place in the highest part of the village, which seems immune to the signs of time. It consists of two rectangular buildings, surrounded by its ancient sloping walls. Today it houses the quarterdeck of the offices of the Municipality.
The Castle of Montano
Monternano was one of the most powerful and vast castles of the Val d’Elsa, donated in 1089 by the Countess of Mingardo Morando to a certain Giovanni of Benzo. It passed from them to the Sienese family Squarcialupi. The position of Monternano (formerly known as Montennana), on the border between the territories of the Republics of Siena and Florence, was a strategic place of great importance along the southern side of the mountains that descend from Chianti to the Val d’Elsa, above the medieval via Francigena and the road Giogoli in Chianti Senese. Together with the nearby Poggibonsi it was an impregnable barrier against the Florentine southward incursions. In 1201 the army attacked Monternano and inflicted a tremendous damage to it, but it was in 1220, with the excuse that some merchants from Florence had been robbed by the Squarcialupi family, that the mighty fortress was conquered and almost razed to the ground.
Rocca di Castellina in Chianti
It is a massive building that stands on the main square with a Fourteenth-century crenellated (merloned) tower from whose top you can admire a unique Chianti countryside. Inside you will find a small Etruscan museum.
This area of Chianti was inhabited since ancient times. Based on recent excavations, it seems that an Etruscan dwelling existed between Vico and Salivolpe, a village a few hundred meters away from the town of Castellina. This hypothesis is corroborated by the discovery of four hypogean tombs of the VII-VI century BC on the hill of Montecalvario. Later the area became home to a Roman dwelling then destroyed during the invasions of the Gauls.
In the eleventh century Castellina was appointed as a settlement dependent on the nearby Castel Trebbio (corresponding to today’s Trebbia, a fraction of Radda in Chianti) under the control of the Guidi, to whom we owe the Construction of the first fortifications. In 1193 the castle passed under the Florentines. In 1250 Castellina joined the League of Chianti, and subsequently became the capital of one of the Terzieri (the other two were headed by Radda and Gaiole) in which the league was divided.
It is known that Siena and Florence waged war against each other during the entire middle ages for supremacy. Castellina, a domain on the road that connected the two cities, was a major Florentine stronghold, therefore strategically very important. But in 1397 the castle was destroyed by the troops of the duke of Milan, allied with the Sienese. A few years later, in 1400, the Florentine Republic decided to strengthen its defenses building a wider circle of massive walls, with a hexagonal shape, interspersed with many square towers, with two doors, one towards Siena and the other towards Florence, crowned at the highest point of the village by a massive rectangular crenellated tower with walls and slopes. Large portions of walls and towers still surround the town (although in several points they are included in home buildings). Sadly, the two city doors no longer exist, as the one opening towards Florence was destroyed during World War II. The main tower in the center of Castellina is still in perfect shape thanks to a painstaking restoration. This series of powerful fortifications passed the acid test in 1452 resisting for 44 days to the siege of the Duke of Calabria. It seems that in this period Castellina had been strengthened even further by the great architect Giuliano da Sangallo Mediceo. Nevertheless, in 1478 the castle capitulated under the attack of the Aragonese and was half destroyed and sacked. In 1483 Castellina eventually went under the power of Florence. In 1774 the League of Chianti was abolished and the territory of the new ‘Community of Castellina’, created under the reforms desired by the Grand Duke Peter Leopold, went under the province of Siena.
A short but tragic event of war saw Castellina in Chianti as a protagonist in 1944, when the retreating German troops chose to build the defense line along the rough land of Castellina. This caused dozens of deaths among the civilian population and considerable destruction.
Road map to Castellina in Chianti:
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