Discovering the Chianti Mountains

A looped itinerary among the Monti del Chianti (“Chianti Mountains”) through picturesque Tuscan villages. The route extends some 46.6 miles (75 kilometers) and can even be completed over 2 days, with an overnight stay in Castellina in Chianti.

Set out from the village of Monti, in the territory of Radda in Chianti, with the first stretch perfect for warming up the muscles in anticipation of the climb to San Sano. This village is known for the monument of the ‟Rana Beona,” a sculpture representing a frog drinking wine, commissioned by local teacher, writer and historian Ferdinando Anichini and created by Plinio Tammaro in 1967. The route then continues along a small country road before climbing back up to Lecchi. 

From here, between the ups and downs, there are detours to Ama (home to an important winery) and Montebuoni. You then reach Radda in Chianti, the ancient capital of the Lega del Chianti (League of Chianti).  

From Radda, set out again by climbing up to Colle Petroso to get to Castellina in Chianti, an ideal place to stop to break the itinerary into 2 days. 

Especially since it is from here that the most challenging part of the route begins!  

After reaching Pietrafitta begins the first ascent to Lucarelli, a small village made famous by gold seekers along the Pesa River. Arriving in Radda in Chianti once more at the end of a long climb, continue past Gaiole in Chianti to the Castello di Meleto. From here, the route descends to the junction leading to the famous Castello di Brolio, goes past Cacchiano then returns to Monti.

The route can also be followed starting from Radda in Chianti and Castellina in Chianti.