The history of the Chianti region is dominated by the rivalry between the cities of Florence and Siena. Italy has existed as a unified country only since the 1860’s and its history up until that time saw a constantly shifting sea of alliances and wars between its prominent city-states. Chianti was the border territory between the commercial power of Florence and the strong democratic government of Siena, and until the 16th century, control of Chianti passed back and forth on a regular basis. Siena aligned itself with the Holy Roman Emperor and Florence with the Pope, so armies from all over the Italian peninsula and other parts of Europe did battle in the Chianti countryside. Villages like Castagnoli were fortified and hilltop military strongholds, like Poggio Rudolfo whose ruin still looks down over Gaiole, were established to keep watch and house troops.
The villages of Gaiole, Radda and Castellina banded together to form the Chianti League, which initially served as a political and military alliance and then became the first official home of Chianti wine. The Black Death struck Siena in 1348, wiping out the majority of the population and leaving the city permanently weakened as it finally came under the long-term control of Florence in 1555.
Chianti rose to prominence again during the campaign to unify Italy in the 1860’s, as Bettino Ricasoli, whose family had been, and still is, based at Castello di Brolio for centuries, was one of the leaders of the Risorgimento movement and became the second Prime Minister of Italy. During World War II, the region again became a battleground between Italian partisans and the retreating troops of the Fascist government and its German allies. This period is beautifully documented in the must-read war diaries of Iris Origo, an American heiress who married an Italian nobleman.