How to get around Gaiole in Chianti

Getting around

Gaiole has no railway station and everything arrives by road. The town sits on the valley floor at 356 metres, where the routes between the Chianti and the upper Valdarno meet — the junction that made it a market in the first place.

In the town, it is one street. The heart of Gaiole is the street-square of via Ricasoli, and the comune itself is at via Ricasoli 5. Everything civic is on it.

Everything else needs the car. 128.99 square kilometres, sixteen frazioni from Lecchi at 421 metres to Montegrossi at 639, and a Strada dei Castelli that exists precisely because the castles are spread across the hills. Meleto is about two kilometres out; Brolio is further south, near San Regolo.

Bicycles are a serious mode here, not a novelty. The strade bianche are the reason the Eroica exists, and on the first Sunday in October they carry a very large field.

For anything municipal, the comune's switchboard is 0577 744711 and it runs a freephone line on 800 012661.

Verified against Comune di Gaiole in Chianti, October 2026.

Driving. Gaiole lies at the junction between the Chianti and the Valdarno superiore, bordering Cavriglia, Montevarchi and Bucine on the Arezzo side and Castelnuovo Berardenga and Radda on the Sienese. Approaches from the Valdarno descend; approaches from Radda and Castellina come over the ridges.

The Strada dei Castelli. The Castle Road winds through the hills and links the comune's fortifications. Along it: Cacchiano, thirteenth-century, destroyed by the Aragonese in 1478 and rebuilt in 1530; Monteluco, near the Massellone, in two nuclei with a lower outpost and a summit complex entered by an elegant arch; the tower of Tornano across the river; and Meleto, about two kilometres before Gaiole.

Brolio. South of the town in the locality of Brolio, near San Regolo, on a spur of the Monti del Chianti between Monte Fienali and Monte Luco Berardenga, flanked by the Malena and Dudda torrents.

Coltibuono. North-east of the town at Badia a Coltibuono, in the former piviere of San Pietro in Avenano.

By bicycle. The white roads are the point. On the first Sunday in October they are closed in spirit if not in law, and the Eroica publishes parking, traffic arrangements and a free shuttle service for the day.

Municipal contacts. Comune di Gaiole in Chianti, via Ricasoli 5, 53013; switchboard 0577 744711; freephone 800 012661; the URP on 0577 744743.

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Sources & verification Covers the sourced claims on this page.

Checked against Comune di Gaiole in Chianti — The Comune di Gaiole in Chianti has its seat at via Ricasoli 5, 53013 Gaiole in Chianti (SI), with a switchboard on 0577 744711, a freephone number on 800 012661 and the certified address comune.gaioleinchianti@postacert.toscana.it; it lists thirteen offices, among them the URP on 0577 744743, Lavori Pubblici e Protezione Civile on 0577 744744, the Polizia Municipale on 0577 744723 and 0577 744737, and the SUAP on 0577 744738, 0577 744739 and 0577 744743., The Comune di Gaiole in Chianti has its seat at via Ricasoli 5, 53013 Gaiole in Chianti (SI), with a switchboard on 0577 744711, a freephone number on 800 012661 and the certified address comune.gaioleinchianti@postacert.toscana.it; it lists thirteen offices, among them the URP on 0577 744743, Lavori Pubblici e Protezione Civile on 0577 744744, the Polizia Municipale on 0577 744723 and 0577 744737, and the SUAP on 0577 744738, 0577 744739 and 0577 744743. (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., The area of Gaiole is crossed by a Castle Road, the Strada dei Castelli, which winds through the hills and allows the visitor to see important testaments to the fortification of the Chianti in the Middle Ages; among these the castle of Cacchiano, built in the thirteenth century by the Ricasoli family, destroyed by the Aragonese in 1478 and rebuilt in 1530; the Monteluco castle a few kilometres from the village near the Massellone stream, consisting of two nuclei, an outpost at the bottom with a mighty stone tower and a large complex on the summit accessed through an elegant arch, with the large tower of Tornano on the opposite side across the river; and, two kilometres before Gaiole, the castle of Meleto, whose current building is an almost square shape with an older tower in the centre and two cylindrical towers perhaps from the 15th century at the south and east corners, the rest having been transformed into a villa in the mid-18th century, and which has a small theatre where the Ricasoli hosted operettas and concerts., The area of Gaiole is crossed by a Castle Road, the Strada dei Castelli, which winds through the hills and allows the visitor to see important testaments to the fortification of the Chianti in the Middle Ages; among these the castle of Cacchiano, built in the thirteenth century by the Ricasoli family, destroyed by the Aragonese in 1478 and rebuilt in 1530; the Monteluco castle a few kilometres from the village near the Massellone stream, consisting of two nuclei, an outpost at the bottom with a mighty stone tower and a large complex on the summit accessed through an elegant arch, with the large tower of Tornano on the opposite side across the river; and, two kilometres before Gaiole, the castle of Meleto, whose current building is an almost square shape with an older tower in the centre and two cylindrical towers perhaps from the 15th century at the south and east corners, the rest having been transformed into a villa in the mid-18th century, and which has a small theatre where the Ricasoli hosted operettas and concerts., On the first Sunday in October the Eroica is held in Gaiole in Chianti; the cycling event winds its way through the white roads that cross the landscapes of the Sienese Chianti, the Crete Senesi and the Val d'Orcia, with an eye to the past, featuring antique bicycles, cyclists in vintage clothing, a range of vintage cars and motorbikes, as well as wine, capocollo and pecorino. (October 2026).
Checked against Eroica — L'Eroica was born in 1997 at Gaiole in Chianti, a small borgo in the province of Siena, where 92 riders set off the first edition of a cycling event that each year combines demanding routes, magnificent landscapes and memorable refreshment stops; the event publishes parking and traffic arrangements and runs a free shuttle service, alongside a register of eroiche bicycles, a bicycle elegance competition, a Mini Eroica and children's cycling, a beard and moustache competition, a shop-window contest, an Eroica Academy and a sustainability manual., L'Eroica was born in 1997 at Gaiole in Chianti, a small borgo in the province of Siena, where 92 riders set off the first edition of a cycling event that each year combines demanding routes, magnificent landscapes and memorable refreshment stops; the event publishes parking and traffic arrangements and runs a free shuttle service, alongside a register of eroiche bicycles, a bicycle elegance competition, a Mini Eroica and children's cycling, a beard and moustache competition, a shop-window contest, an Eroica Academy and a sustainability manual. (October 2026).