Gaiole in Chianti historical timeline

History

Gaiole exists because two roads met. Its history is strictly tied to its position as a road junction in the communications between the Chianti and the upper Valdarno, and it was that which made it the seat of the market of the neighbouring castles.

The first mention is 1086. It appears in a charter of the Badia a Coltibuono, and at that period the inhabitants of the nearby castles of Vertine, Montegrossi and San Donato in Perano began to meet on the valley floor, along the Massellone torrent, to exchange goods. Initially the market stood at the foot of the castle of Barbischio. Gaiole's market is cited in notarial acts from 1215.

The land was older than the market. The area was already known and inhabited in Etruscan and Roman times, as the place names deriving from ancient languages show, along with the remains of the necropolis at Cacchiano of the 1st–3rd century CE and the columns of the pieve di San Marcellino a Monti, typical of the imperial age and most probably taken from an earlier Roman building.

In the fourteenth century Gaiole and its community entered the Lega del Chianti, and in the fifteenth it became the capital of its terziere — one of the three, with Radda and Castellina. A commercial centre that was now also a defensive strongpoint on the Florence–Siena border, it was harried by continuous raids until 1555, when Siena surrendered and the territory was annexed to the Grand Duchy of Tuscany.

The market outlasted the wars. Still in the eighteenth century the market of Gaiole was an important event for the area, as Grand Duke Pietro Leopoldo testified in his reports after the visit he made in July 1773.

Then it changed province. Until the beginning of the nineteenth century Gaiole belonged administratively to the province of Florence, but in the Napoleonic era, during the Kingdom of Etruria, it was inserted into the Sienese Department and into the province of Siena, where it remains. Bettino Ricasoli was mayor for many years.

In 1860 it declined to vote itself into Italy. At the plebiscite on the annexation of Tuscany to the Kingdom of Sardinia the "yes" votes did not obtain the majority of those entitled, with a record abstention — a symptom of opposition to the annexation.

The modern story is emptying and refilling. After the Second World War the communal territory was struck by the depopulation of the countryside, but from the end of the 1970s the former farmhouses have been progressively restored and today host agriturismi, and enogastronomic tourism is the principal source of wealth for the territory.

Verified against Wikipedia, October 2026.

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Checked against Wikipedia — The history of Gaiole in Chianti is strictly tied to its position as a road junction in the communications between the Chianti and the upper Valdarno; thanks to this it became the seat of the market of the neighbouring castles. Its first record is found in a charter of the Badia a Coltibuono going back to 1086, and at that period the inhabitants of the nearby castles of Vertine, Montegrossi and San Donato in Perano began to meet on the valley floor, along the Massellone torrent, to exchange goods; initially the market was situated at the foot of the castle of Barbischio. The market of Gaiole is cited in notarial acts from 1215., In the 14th century Gaiole and its community entered the Lega del Chianti, and still in the 18th century the market of Gaiole was an important event for the area, as Grand Duke Pietro Leopoldo testified in his reports following the visit he made in July 1773. Until the beginning of the 19th century Gaiole belonged administratively to the province of Florence, but in the Napoleonic era, during the Kingdom of Etruria, it was inserted into the Sienese Department and in the province of Siena it remains to this day. For many years Bettino Ricasoli was its mayor., At the plebiscite of 1860 for the annexation of Tuscany to the Kingdom of Sardinia the "yes" votes at Gaiole did not obtain the majority of those entitled to vote, with a record abstention, a symptom of opposition to the annexation., After the Second World War the communal territory of Gaiole was struck by the phenomenon of rural depopulation, but from the end of the 1970s the former farmhouses have been progressively restored and are today the seat of agriturismi, and enogastronomic tourism is the principal source of wealth for the territory. In the comune cemetery is the tomb of Carla Lonzi, historian and art critic, philosopher and founder in 1970 of Rivolta Femminile. (October 2026).
Checked against Visit Tuscany (Toscana Promozione Turistica) — Founded between the 13th and 14th centuries, Gaiole was established as a merchant town serving the many castles dotting the surroundings; the area was already known and inhabited in the Etruscan and Roman periods, as highlighted by place names deriving from ancient languages, the ruins of the necropolis at Cacchiano of the 1st-3rd century CE and the columns of the parish church of San Marcellino at Monti, typical of the imperial age and most likely taken from an earlier Roman building. In the 1400s Gaiole became the capital of the terziere within the Lega del Chianti and, previously a commercial centre and now also a defence stronghold on the border between Florence and Siena, was oppressed during continuous raids until 1555, when Siena surrendered and the town was annexed to the Grand Duchy of Tuscany. For centuries the heart of Gaiole has been the street-square, via Ricasoli, a place of trading and daily life, and the main church of the town is dedicated to San Sigismondo, a neo-Gothic construction covered in pietra serena except for the facade. (October 2026).