Castellina in Chianti historical timeline

History

Castellina is a frontier post that stopped being a frontier. For three centuries it was Florence's most exposed outwork on the most direct road to Siena — fortified on Brunelleschi's advice, besieged twice, burnt once and held by the enemy for five years. Then the border moved, and a town built entirely for war became the seat of a rural comune and, eventually, of a wine zone.

Chronology

7th-6th c. BC The Etruscans. The tumulo di Montecalvario and the necropoli del Poggino near Fonterutoli attest them, and excavation from the 1980s showed a settlement of notable size at Salingolpe, a few hundred metres away. These were the lords who controlled the routes following the watercourses — the Arbia, the Ombrone, the Pesa and the Greve.
11th century The written record begins. The area is a fief of the nobles of the Castello del Trebbio, a family connected to the conti Guidi, and the place is called Castellina de' Trebbiesi.
12th century It passes under Florence.
1193 The lords of Trebbio agree that the Florentines may garrison Trebbio and Castiglione — the Castellina of today.
1203 The Lodo di Poggibonsi fixes the Chianti boundary between Florence and Siena, and leaves Castellina one of the most important Florentine outposts, on the most direct road between the two.
14th century It heads one of the three terzieri of the Lega del Chianti, administering the part of Chianti that falls away towards the Valdelsa.
1397 Sacked and burnt entirely by the troops of Gian Galeazzo Visconti, duke of Milan, under Alberico da Barbiano, allied to Siena.
1400 Florence resolves to fortify the place. The register of riformagioni in the Archivio di Stato di Firenze reads in loco qui dicitur la Castellina fiat fortilitia. Building begins the following year.
1430 The Opera del Duomo's workmen are charged with the works, and Filippo Brunelleschi is sent to specify them and estimate the cost.
1452 The new defences hold. The garrison sees out a siege of 44 days.
1478 They do not hold a second time. Castellina falls to Sienese and Neapolitan troops, with Giuliano da Sangallo directing the defence and Francesco di Giorgio Martini commanding the besiegers.
1483 The Sienese, who had held the place since the fall, give it up.
1774 The frontier stops mattering. Grand Duke Pietro Leopoldo's reform makes Castellina the seat of a Comunità, the ancestor of the modern comune, drawn to coincide almost exactly with the old terziere.

Verified against Wikipedia, October 2026.

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Sources & verification Covers the sourced claims on this page.

Checked against Wikipedia — The tumulo di Montecalvario, an Etruscan tomb near the inhabited centre dated to the 7th-6th century BC, and the necropoli del Poggino near Fonterutoli attest the presence of the Etruscans in the area; excavation campaigns carried out from the 1980s established a settlement of notable size in the locality of Salinvolpe, a few hundred metres from today's Castellina., The first certain documents go back to the 11th century, when the area was a fief of the nobles of the Castello del Trebbio, a family related to the conti Guidi; in the 12th century Castellina passed under the influence of Florence, and in 1193 an accord was signed between the lords of Trebbio and Florence conceding to the Florentines the right to garrison militarily the castles of Trebbio and of Castiglione, today's Castellina., After the Lodo di Poggibonsi of 1203, the act in which the Chianti boundaries between Florence and Siena were established, Castellina found itself one of the most important Florentine outposts, since it lay on the most direct road putting the two rival cities in communication., In the 14th century Castellina became one of the strongholds of the Lega del Chianti, to the point of heading one of the terzieri into which it was divided; the Terziere di Castellina administered the part of Chianti that slopes down towards the Valdelsa., In 1397 Castellina was sacked and entirely burnt by the troops of the Duke of Milan Gian Galeazzo Visconti, commanded by Alberico da Barbiano., In 1400 it was decided to fortify Castellina, and in the list of riformagioni preserved at the Archivio di Stato di Firenze is written "in loco qui dicitur la Castellina fiat fortilitia"; in 1430 the workmen of the Opera del Duomo were charged with fortifying Castellina together with Staggia Senese and Rencine, and Filippo Brunelleschi was sent to establish the kind of interventions needed and to make an estimate of the costs., The baptism of fire of the new defensive system came in 1452, when Castellina was besieged for a full 44 days without being taken., In 1452 the walls of Castellina withstood the assault of the Aragonese troops; in 1478, during the second Aragonese invasion of the Chianti, Castellina was conquered by Sienese and Neapolitan troops, with the defence directed personally by Giuliano da Sangallo and the besiegers commanded by Francesco di Giorgio Martini, and the Sienese occupation lasted until 1483, when the Florentines retook it., In 1774, with the administrative reform of Grand Duke Pietro Leopoldo, Castellina became the seat of a Comunita, from which the present comune derives. (October 2026).
Checked against Museo Archeologico del Chianti senese — The orientalising period, 720-580 BC, is marked in Etruria by the acquisition of luxurious products and cultural models expressing the splendour of the courts of the Near East; the new Etruscan lords controlled the transit routes following the watercourses, and the reliefs of the Chianti were involved in that network because they are innervated by the significant watercourses that rise there -- the Arbia, the Ombrone, the Pesa and the Greve -- as the aristocratic burials of the tumulo di Montecalvario at Castellina, of Malpensata at Radda, of the Poggino at Fonterutoli and of the Poggione at Castelnuovo Berardenga show. (October 2026).