The Palio

kilometres: 90

How to reach

from Siena take the SS 222 and after about 17 km you arrive at Castellina in Chianti.

Castellina in Chianti

It’s a quiet and peaceful village full of old buildings, up on a hill at 578 mt high; it is set amidst the countryside of vine-yards, olive plantations and oak-woods. In XIIIth century, together with Radda and Gaiole, it was a member of Lega del Chianti, whose flags had the famous black cock, that became symbol of Classic Chianti Wine. The town preserves the typical thirteenth century plan: the beautiful castle, which now houses the Town Council, and the unique Via delle Volte, a street almost totally sheltered by vaults. Buildings such as churches, castles and farms are spread all over the charming surroundings of Castellina. There are many complexes that offer accommodation in a very friendly atmosphere typical of farmohouse holiday or elegant country lodges.

Leaving Castellina in Chianti take the SS 429, the heart of the sienese chianti, to Radda in Chianti.

Radda in Chianti

It is situated on a little hill separating the Val di Pesa from the Val d'Arbia. In the 1400s it was made into a florentine fortress and subsequently it became chief town of the Chianti league. The ruins of the ancient defensive walls and look-out towers are all that remains of that period.

Take the road to Firenze and after about 2 km turn right to Volpaia.

Volpaia

It was recorded for the first time in 1772 in a document from the Abbey of San Lorenzo a Coltibuono as the "Curte et Castello di Vulpaia". The original defense walls, laid with great precision out of local pietra arenaria (sandstone), date back to the end ofthe XII and beginning of the XIII centuries. It was not until the first half of the XIV century however, when the castle became one of the main centers of the Lega del Chianti, the Chianti League, in the Radda area, that it assumed a role of any real importance. Because of its favourable and dominative position it was soon equipped with a true surrounding wall in the form of a rough ellipse with the defense towers rising up in a quadrangular arrangement. Today only a part of this wall and a small later-dated tower to the north are still visible. There is no trace of the gate which probably corresponded in the defense wall with the street dividing the area into two parts. Only gradually-especially around 1500 to 1600 - did the castle lose its purely defensive function, new gates then being constructed. The parish church, dedicated to San Lorenzo since the XIV century, has a sextangular arch. At the summons of the castle lord the Commenda di San Eufrosino was established in 1443 outside the gare of the ancient castle, in order to shelter and provide care for pilgrims and wayfarers. The site of the hospital is indicated by a Maltese cross carved under an architrave. The edifice shows characteristics of the early FIorentine Renaissance such as the simple rectangular structure and the contrast between the grey of the pietra serena (local grey sandstone) used for the omamental elements and the white of the walls. There were very few buildings outside the surrounding wall and those few were all only mentioned for the first rime at the end of the XVI century.

From Radda in Chianti continue along the SS 429 which after 7 km become SS 408, Siena Montevarchi, near Badia a Coltibuono.

Badia a Coltibuono

Or the "abbey at the good harvest" was founded by Vallombrosini monks around one thousand years ago. For several years now Coltibuono has offered groups of visitors the opportunity, by appointment, to visi the thousand-year-old cellars excavated underneath the walls of the interior cloister. The tour always ends with a guided tasting of the fattoria' s wines. In the restaurant at Coltibuono guests can savour the foods and wines of the Chianti land. Aside from wine and the best Chianti products the cantina, cellar, also offers other vintage ltalian labels. At the shop located in the old "Osteria" you can buy -but it more expensive- Chianti Classico and Riserva, Chianti Cetamura, Sangioveto and Sella del Boscone, extra virgin olive oil, Vinsanto, vinegar and honey.

From Badia a Coltibuono take the SS 408 to and after less of 5 km you are in Gaiole in Chianti.

Gaiole in Chianti

During the Middle Ages it was an important market place, developed along the road for Valdarno. The numerous castles and parish churches in the vicinity bear witness to an intense and prosperous agricultural and commercial activity.

From Gaiole in Chianti continue on the SS 408 to Siena. After less of 3 km turn left to Castagnoli and then turn right to Castello di Meleto.

Castello di Meleto

It is one of the most famous castles of the Chianti.The castle, turned into a villa with spacious rooms painted in fresco and a small theatre, during the 18th century, still has a massive square watch tower and two circular towers on the southern-side. It now houses a wine production business.

Go back on the road to Castagnoli and when you arrive there turn right to San Martino: the road, with many bends, go down for 3 km till to arrive at the SS 484 which unites the SS 408 with Castelnuovo Berardenga. Turn left, direction Castelnuovo, and go uo for other 3 km till Brolio.

Castello di Brolio

It is the most famous fortification of the Chianti. We get to the magnificent complex through an avenue flanked with cypresses in a beautiful park .The fifteenth-century walls, of an irregular pentagonal shape, are about 500 metres in perimeter and have big bastions from where several embrasures open. One of the underground paths can be still used. Ricasoli, creator of the famous Chianti wine Chianti commissioned Pietro Marchetti to build the country-palace, a building in red brick with a tower and battlements in the neo-gothic style. The fourteenth-century chapel of St.Jacopo with the tombs of the Ricasoli is inside.
For lovers of wine I recommend the visit and the tasting of Chianti at Barone Ricasoli.

From Castello di Brolio take again the SS 484 to Castelnuovo Berardenga and stop at San Gusmè.

San Gusme'

The beautiful village of S.Gusmè - from the names of the saints of the local church, Cosma and Damiano - is a typical medieval group of houses with thirteenth-century walls. It was an important Sienese fortress, often exposed to attacks and sieges till its fall in 1554. The village, with the remains of the walls and its two gates with arches and coats of arms, has maintained much of its medieval appearance.

From San Gusmè after 5 km you are at Castelnuovo Berardenga.

Castelnuovo Berardenga

It's the most southern commune in Chianti. Castelnuovo belonged to the Berardenga family. In 1260 at Montaperti (which lies in Castelnuovo), there was a fight in which the Guelfi beat the Ghibellini. One should see in the town: the Tower of the XVIth cent. and the Villa Chigi Saracini from the XVIIIth century. On the outskirts of the town, one should see the castle of Montalto located in Vagliagli, in the heart of the Chianti Classico, and the XVIth cent. Fortezza dell'Aiola.

Leave Castelnuovo Beradenga following direction to Pianella where you arrive again on the SS 408 Siena-Montevarchi. After 2 km and half you find the pieve of Pàcina. From you can arrive at Montaperti.

Monteaperti

Historic battlefield where Siena defeat Firenze on 4th September 1260.

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Last-Tour » Siena » Getting to » Places to sleep » Place to eat » Things to see »Tour of the Chianti area » The Palio

kilometres: 90

How to reach
from Siena take the SS 222 and after about 17 km you arrive at Castellina in Chianti.
Castellina in Chianti
It’s a quiet and peaceful village full of old buildings, up on a hill at 578 mt high; it is set amidst the countryside of vine-yards, olive plantations and oak-woods. In XIIIth century, together with Radda and Gaiole, it was a member of Lega del Chianti, whose flags had the famous black cock, that became symbol of Classic Chianti Wine. The town preserves the typical thirteenth century plan: the beautiful castle, which now houses the Town Council, and the unique Via delle Volte, a street almost totally sheltered by vaults. Buildings such as churches, castles and farms are spread all over the charming surroundings of Castellina. There are many complexes that offer accommodation in a very friendly atmosphere typical of farmohouse holiday or elegant country lodges.
Leaving Castellina in Chianti take the SS 429, the heart of the sienese chianti, to Radda in Chianti.

Radda in Chianti
It is situated on a little hill separating the Val di Pesa from the Val d'Arbia. In the 1400s it was made into a florentine fortress and subsequently it became chief town of the Chianti league. The ruins of the ancient defensive walls and look-out towers are all that remains of that period.

Take the road to Firenze and after about 2 km turn right to Volpaia.

Volpaia
It was recorded for the first time in 1772 in a document from the Abbey of San Lorenzo a Coltibuono as the "Curte et Castello di Vulpaia". The original defense walls, laid with great precision out of local pietra arenaria (sandstone), date back to the end ofthe XII and beginning of the XIII centuries. It was not until the first half of the XIV century however, when the castle became one of the main centers of the Lega del Chianti, the Chianti League, in the Radda area, that it assumed a role of any real importance. Because of its favourable and dominative position it was soon equipped with a true surrounding wall in the form of a rough ellipse with the defense towers rising up in a quadrangular arrangement. Today only a part of this wall and a small later-dated tower to the north are still visible. There is no trace of the gate which probably corresponded in the defense wall with the street dividing the area into two parts. Only gradually-especially around 1500 to 1600 - did the castle lose its purely defensive function, new gates then being constructed. The parish church, dedicated to San Lorenzo since the XIV century, has a sextangular arch. At the summons of the castle lord the Commenda di San Eufrosino was established in 1443 outside the gare of the ancient castle, in order to shelter and provide care for pilgrims and wayfarers. The site of the hospital is indicated by a Maltese cross carved under an architrave. The edifice shows characteristics of the early FIorentine Renaissance such as the simple rectangular structure and the contrast between the grey of the pietra serena (local grey sandstone) used for the omamental elements and the white of the walls. There were very few buildings outside the surrounding wall and those few were all only mentioned for the first rime at the end of the XVI century.
From Radda in Chianti continue along the SS 429 which after 7 km become SS 408, Siena Montevarchi, near Badia a Coltibuono.

Badia a Coltibuono
Or the "abbey at the good harvest" was founded by Vallombrosini monks around one thousand years ago. For several years now Coltibuono has offered groups of visitors the opportunity, by appointment, to visi the thousand-year-old cellars excavated underneath the walls of the interior cloister. The tour always ends with a guided tasting of the fattoria' s wines. In the restaurant at Coltibuono guests can savour the foods and wines of the Chianti land. Aside from wine and the best Chianti products the cantina, cellar, also offers other vintage ltalian labels. At the shop located in the old "Osteria" you can buy -but it more expensive- Chianti Classico and Riserva, Chianti Cetamura, Sangioveto and Sella del Boscone, extra virgin olive oil, Vinsanto, vinegar and honey.
From Badia a Coltibuono take the SS 408 to and after less of 5 km you are in Gaiole in Chianti.
Gaiole in Chianti
During the Middle Ages it was an important market place, developed along the road for Valdarno. The numerous castles and parish churches in the vicinity bear witness to an intense and prosperous agricultural and commercial activity.
From Gaiole in Chianti continue on the SS 408 to Siena. After less of 3 km turn left to Castagnoli and then turn right to Castello di Meleto.

Castello di Meleto
It is one of the most famous castles of the Chianti.The castle, turned into a villa with spacious rooms painted in fresco and a small theatre, during the 18th century, still has a massive square watch tower and two circular towers on the southern-side. It now houses a wine production business.
Go back on the road to Castagnoli and when you arrive there turn right to San Martino: the road, with many bends, go down for 3 km till to arrive at the SS 484 which unites the SS 408 with Castelnuovo Berardenga. Turn left, direction Castelnuovo, and go uo for other 3 km till Brolio.

Castello di Brolio
It is the most famous fortification of the Chianti. We get to the magnificent complex through an avenue flanked with cypresses in a beautiful park .The fifteenth-century walls, of an irregular pentagonal shape, are about 500 metres in perimeter and have big bastions from where several embrasures open. One of the underground paths can be still used. Ricasoli, creator of the famous Chianti wine Chianti commissioned Pietro Marchetti to build the country-palace, a building in red brick with a tower and battlements in the neo-gothic style. The fourteenth-century chapel of St.Jacopo with the tombs of the Ricasoli is inside. For lovers of wine I recommend the visit and the tasting of Chianti at Barone Ricasoli.
From Castello di Brolio take again the SS 484 to Castelnuovo Berardenga and stop at San Gusmè.
San Gusme'
The beautiful village of S.Gusmè - from the names of the saints of the local church, Cosma and Damiano - is a typical medieval group of houses with thirteenth-century walls. It was an important Sienese fortress, often exposed to attacks and sieges till its fall in 1554. The village, with the remains of the walls and its two gates with arches and coats of arms, has maintained much of its medieval appearance.
From San Gusmè after 5 km you are at Castelnuovo Berardenga.
Castelnuovo Berardenga
It's the most southern commune in Chianti. Castelnuovo belonged to the Berardenga family. In 1260 at Montaperti (which lies in Castelnuovo), there was a fight in which the Guelfi beat the Ghibellini. One should see in the town: the Tower of the XVIth cent. and the Villa Chigi Saracini from the XVIIIth century. On the outskirts of the town, one should see the castle of Montalto located in Vagliagli, in the heart of the Chianti Classico, and the XVIth cent. Fortezza dell'Aiola.
Leave Castelnuovo Beradenga following direction to Pianella where you arrive again on the SS 408 Siena-Montevarchi. After 2 km and half you find the pieve of Pàcina. From you can arrive at Montaperti.
Monteaperti
Historic battlefield where Siena defeat Firenze on 4th September 1260.

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