Volpaia historical timeline

It was built where it is for one reason. The castle probably arose around the 10th century, on the crest of a hill running from the Badia a Montemuro towards Radda, because standing on the watershed of two small valleys formed by tributaries of the Pesa it was easily defensible — a precious quality in an age that the settling of feudal society had made deeply insecure.

Its strategic position was doubly important because it was frontier land, between Florence and Siena. Politically the fortified borgo fell, with the nearby pieve di Santa Maria Novella, within the judicaria florentina from the eleventh century, though it is certainly included in Florentine-dependent territory only from the second half of the twelfth, when the first boundary settlements between the Sienese and Florentine republics were made. So when Florence organised its territory into autonomous jurisdictions called Leagues in 1250, Volpaia fell within the Lega del Chianti, among the peoples of the Terzo di Radda.

That placement decided its church and its roads. Volpaia belonged to the diocese of Fiesole and its church, dedicated to San Lorenzo martire, depended on the pieve di Santa Maria Novella. From that pieve — an important Chianti road junction — a road ran through Volpaia linking the upper Pesa valley with the Valdarno Superiore, which is precisely why a hospital for pilgrims would later be founded here in the fifteenth century.

Then the fifteenth century happened to it. Volpaia repeatedly suffered the consequences of the secular struggle between the Sienese and Florentine republics: above all the raids of the condottiere Alberico da Barbiano during the war between Florence and Filippo Maria Visconti, and the two disastrous Aragonese invasions of 1452 and 1478.

In 1478 it distinguished itself. On 24 December 1477 the Republic of Siena and Ferdinand, king of Naples, allied against Florence; the following year the bloc gained papal blessing when Sixtus IV joined it, angry with the Medici for implicating his nephew, the cardinal of San Giorgio, in the Pazzi conspiracy. In July 1478 the allied army attacked the Florentine state from the Val di Staggia, besieged the castle of Rencine and soon took it, then in August seized the principal Chianti strongholds, Volpaia among them. Because the League's third and sixth articles laid down that all lands and castles taken within fifteen miles of Siena should belong to the Sienese, Volpaia seemed bound for the enemy camp. Instead, before August was out Volpaia rebelled against the Sienese who had taken possession of it, drove out the garrison set to guard it, and took the Sienese commissioner, named Cipriano, prisoner to Florence.

The reprisal was immediate and the recovery quick. Warned of the revolt, the allied army came up with Federico, son of the king of Naples, at the head of many troops, and on 2 September, overcoming the defenders' resistance, stormed the castle again. It was not a lasting conquest: on 7 October of the same year the Florentines retook it, as they did most of the Chianti castles. The war moved out of the Chianti and ran on until the truce agreed at Rome in 1479, made peace in March 1480.

Peace dismantled it. A turning point came in the sixteenth century with the decline of Sienese power, which led in 1555 to the fall of the republic. A long period of peace began for the Chianti, and Volpaia, its defensive function gone, slowly lost its warlike aspect: long stretches of wall disappeared and dwellings were built in their place.

• Wikipedia