
Castelnuovo Berardenga and the castles of Chianti
The Chianti Classico closest to the Grancia: a fortified Sienese village, two castles among the vineyards, Gaiole and Radda.
Siena and Chianti · castles, wine, villages
- km in all
- 109
- of driving
- 2 h 25
- the whole day, stops included
- 5 h
- stops
- 5
From Serre you climb towards Chianti by way of Castelnuovo Berardenga, and the road to Brolio runs through San Gusmè and Villa a Sesta. It is the tour with the most driving, all on hill roads: we suggest setting off early, so you have time to enjoy the stops.
The day
Driving times are Google Maps' without traffic; the stops are the ones we suggest. Leave around 9 and you will be back in the early afternoon.
Leave the Grancia
20 min by car · 20 km
Castelnuovo Berardengasuggested stop about 25 min
25 min by car · 13 km
Brolio Castlesuggested stop about 50 min
20 min by car · 11 km
Gaiole in Chiantisuggested stop about 25 min
10 min by car · 3.1 km
Castello di Meletosuggested stop about 15 min
15 min by car · 10 km
Radda in Chiantisuggested stop about 40 min
55 min by car · 53 km
Back at the Grancia
The stops
from La Grancia · 20 km · about 20 min
Castelnuovo Berardenga

Chianti Classico DOCG
The castle was founded by Siena after a decision of 1366, as an outpost facing Florence, and today Castelnuovo is the southernmost municipality of Chianti Classico. In the village, the Propositura of Saints Justus and Clement and Villa Chigi Saracini, with its park, are worth a stop.
- the historic centre
- the Propositura of Saints Justus and Clement
- Villa Chigi Saracini
from Castelnuovo Berardenga · 13 km · about 25 min
Brolio Castle

Chianti Classico DOCG
On the way you drive through San Gusmè, a small village with its walls almost intact, and Villa a Sesta. The castle has belonged to the Ricasoli family since a deed of 1141 and was remodelled in Gothic Revival style from 1835. Here Bettino Ricasoli worked out the recipe of Chianti, which the Ricasoli estate dates to 1872. The castle, the gardens and the Ricasoli Collection can be visited for a fee: seasons and hours at ricasoli.com.
- the gardens
- the Ricasoli Collection
- the view over the vineyards
from Brolio Castle · 11 km · about 20 min
Gaiole in Chianti

Chianti Classico DOCGL'Eroica since 1997
It was part of the Lega del Chianti. It is the home of L'Eroica: the first edition was held here in 1997, and every year, in early October, the vintage bike ride sets off from Gaiole along the gravel roads.
- the village
- the gravel roads of L'Eroica
from Gaiole in Chianti · 3.1 km · about 10 min
Castello di Meleto

Chianti Classico DOCG
First mentioned in 1256, it has two round towers added after 1480; in the 18th century it became a villa, with a small theatre that still keeps seven original sets. Today it is a wine estate: guided tours, for a fee, include the theatre and the cellars (castellomeleto.it).
- the castle
- the 18th-century theatre, on the guided tour
from Castello di Meleto · 10 km · about 15 min
Radda in Chianti

Chianti Classico DOCG
It was the chief town of the Lega del Chianti, with Gaiole and Castellina, as the statute of 1415 confirms. In the centre stands the 15th-century Palazzo del Podestà, rebuilt after 1478, and stretches of the walls still survive. The Black Rooster, today the symbol of Chianti Classico, was the emblem of the Lega.
- the Palazzo del Podestà
- the walls
- the historic centre
from Radda in Chianti · 53 km · about 55 min
Back to the Grancia
From Radda it is about 45 minutes back to the Grancia.
Why choose it
Brolio and Meleto, two castles among the Chianti Classico vineyards. If you travel by bike, you will find the gravel roads of L'Eroica in Gaiole.
Where to stop
Brolio and Meleto charge for visits and keep their own hours: we suggest checking them before you go and, for Meleto, booking the guided tour.
It is the tour with the most driving, all on hill roads. If you prefer to keep it to half a day, you can skip one stop, for example Meleto.
Distances and times are Google Maps' without traffic and are approximate: traffic, parking and stops add to them.
FAQ
How far is Castelnuovo Berardenga from the Grancia?
About 18 km by car, around twenty minutes.
What is Chianti Classico?
The DOCG wine of the historic Chianti area: it is made in the whole of Castellina, Gaiole, Greve and Radda and in part of Castelnuovo Berardenga, Barberino Tavarnelle, Poggibonsi and San Casciano. Its symbol is the Black Rooster.
Where does L'Eroica start?
In Gaiole in Chianti, where the first edition was held in 1997.
Does the route pass San Gusmè and Villa a Sesta?
Yes, both are on the road between Castelnuovo Berardenga and Brolio: you can stop for a few minutes without a detour.

Set off from the Grancia and come back to it
Four Junior Suites in the old town of Serre di Rapolano: in the evening you come back to the same place, with no need to repack.
Check availability- Photo: opening photo · Eric Kilby, CC BY-SA 2.0, via Wikimedia Commons
- Photo: Castelnuovo Berardenga · LigaDue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Castelnuovo Berardenga, the Propositura of Saints Justus and Clement · Vignaccia76, CC BY 3.0, via Wikimedia Commons
- Photo: Castelnuovo Berardenga, Villa Chigi Saracini · LigaDue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Brolio Castle · Argentieri.Andrea, CC BY-SA 4.0, via Wikimedia Commons
- Photo: San Gusmè, on the way · LigaDue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Villa a Sesta, on the way · LigaDue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Brolio Castle, the gardens · Argentieri.Andrea, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Brolio Castle, the view over the vineyards · Argentieri.Andrea, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Gaiole in Chianti · LigaDue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Castello di Meleto · Vignaccia76, CC BY-SA 3.0, via Wikimedia Commons
- Photo: Castello di Meleto, the 18th-century theatre · sailko, CC BY-SA 3.0, via Wikimedia Commons
- Photo: Radda in Chianti · Kasa Fue, CC BY-SA 4.0, via Wikimedia Commons
- Photo: Radda in Chianti, the Palazzo del Podestà · Pufacz, CC BY-SA 4.0, via Wikimedia Commons







