Landscape view of mountains near Precise House Montaperti Siena

Chianti route

Podere Belvedere Tuscany near Precise House Montaperti Siena

ROUTE FROM SIENA TO CHIANTI (half a day/ 1 day)

Chianti is a vast area in Central Tuscany. Its heart, which produces the famous Chianti Classico, is divided between Siena and Florence.

Once passed the village of Casetta, you take the freeway to Bettole and you exit at Castelnuovo Berardenga. You pass Castelnuovo Berardenga, which still has a tiny historical centre almost destroyed to build Villa Chigi, and you continue to Gaiole in Chianti/ Brolio.

After only 4 km you find a crossroads to S. Gusmè one of the Sienese fortified villages built to protect the town. Only 6 km from here there was the Castello di Brolio, the very last fortress of the Republic of Florence. The castle is situated in commanding position, almost 600 metres above sea level. Its ramparts were planned by Sangallo, whereas the neogothic building was built in the 19th century by pulling down a part of the original Renaissance villa.

On your way from Brolio to Gaiole in Chianti, you can turn to the right to visit the Castello di Meleto characterised by two mighty round towers. Gaiole, unlike Radda or Castellina, was not fortified because it was only a marketplace. The small, fortified village of Vertine is certainly well worth a visit as it has preserved its original mediaeval form.

From Gaiole you can decide to reach Radda turning back towards Siena and then turning to the right at the first crossroads or proceeding uphill to Badia Coltibuono going to Radda after a visit to the abbey. Radda in Chianti, the ancient capital of the Chianti League, is a small, fortified village which developed around S. Niccolò’s church dating back to the 13th century and the Palazzo pretorio. 

From Radda you continue to Castellina in Chianti, another fortified centre along the walls of which runs an ancient sentry walk, Via delle Volte. In the centre of the village there is the Rocca, a keep dating from the 14th century. From Castellina you drive along SS 222 Chiantigiana to come back to Siena.

On your way you can stop at one of the countless wineries of the area to taste wine and other typical products.