Castellina in Chianti and the Via Chiantigiana Towards Siena

Castellina in Chianti stands on a hillock that dominates the Arbia, Pesa and Elsa basins. The unearthing of a 7th-6th century BC burial ground a short distance out of town, on Monte Calvario, has prompted academics to believe that Castellina was in fact originally an Etruscan settlement.

The earliest documents that refer to Castellina date from the 11th century and list it as part of the estate of the Castle of Trebbio, known today as Trebbia, which belonged to the Counts Guidi. In 1200 Castellina joined the Lega del Chianti league of towns, becoming the chief city of one of the terzieri that made up the league.

An important military strategic point during the Middle Ages, Castellina was fiercely contended by Florence and Siena. The frequent incursions into its surrounding domains by Senese troops, who also sacked the town itself on more than one occasion, prompted Florence to considerably reinforce the fortifications of Castellina.

In the 15th century square defence towers were placed along the defence walls, which had only two gateways: one towards Siena and the other towards Florence – neither survive today. The higher part of town has a crenellated rectangular keep that was converted into the town hall in 1927 after undergoing substantial restoration works. One of the most interesting elements of Medieval Castellina to survive remains Via delle Volte, however – a sunken walkway with narrow openings through the walls that afford magnificent views over the surrounding countryside.

One of the main communication routes across Tuscany, the Via Chiantigiana runs between Florence and Siena. Prior to the construction of the motorway that connects these two cities, the Via Chiantigiana was the quickest route from Florence to Siena and remains today one of the best ways of discovering the many artistic and historical treasures of Tuscany.

Travelling southwards along the Via Chiantigiana, after about 20 kilometres from Florence the first important town is Impruneta. Originally an Etruscan settlement that developed further under the Romans, during the Middle Ages Impruneta was one of the focal points of the war between Florence and Siena. Today the town is famed for its wine and oil, but perhaps its best known export is ceramic – a craft that has been alive here for many centuries, as testified by the fact that the entire roof of the dome of the Duomo in Florence is tiled in Impruneta ceramic.

A little further on down the Via Chiantigiana is Greve in Chianti, a small town that developed as a market town as from the 13th century thanks to its strategic position at the crossroads of two of the main roads that led to Florence and Siena. Each year an important market fair of Chianti Classico is held in the main square of Greve.

The Via Chiantigiana then runs along the banks of the river Greve to Panzano, a beautiful old hamlet perched amidst vineyards and olive groves, with an important church and a well-preserved castle. A little further south is Radda in Chianti, which in the Middle Ages was the flagship city of the Lega del Chianti league of towns that included Castellina, Gaiole and Greve. Today the town is the seat of the Consorzio del Chianti Gallo Nero consortium. Its 15th century Palazzo Pretorio, decorated with the coats of arms of the town’s Podestà through the ages, is well worth a visit.

Castellina in Chianti is to the south east of Radda and has become a highly popular international holiday destination. A little further south is Gaiole in Chianti, in an area that is particularly rich in castles and chapels such as the castles of Vertine, Meleto, Barbischio and Brolio – owned by the Ricasoli family and an important Chianti winery. The Romanesque Pieve di Spaltenna is well worth a visit, along with the Abbey of Coltibuono, erected in the 11th century by the Vallombrosa monks.

Still further along the Via Chiantigiana towards Siena, in the southern part of the Chianti, is Castelnuovo Berardenga. This is already in the upper Ombrone basin and the breathtaking landscape of the Crete Senesi is already visible from here. Founded in the 9th century, Castelnuovo Berardenga has a fine old town centre with a 14th century tower known as the Torre dell’Orologio, the Church of St Giusto and St Clemente and the Museo del Paesaggio. Surrounded by magnificent grounds, Villa Chigi Saracini dominates the town from above. As well as for its wine production, Castelnuovo Berardenga is also renowned for its wrought iron.

According to boundaries drawn up in 1929, the Chianti region ends here.