From Pianella to Castelnuovo Berardenga: a journey through the Chianti Senese area

Pianella, a small hamlet in the Chianti Senese hills, is the starting and finishing point of this captivating and quite challenging 58-kilometer loop itinerary.

It is advisable to tackle it is with a gravel bike, a wide-wheeled touring bike or a good quality MTB, due to its dirt roads and significant slopes.  

The journey begins on a paved road that takes you gently uphill to Villa Pagliaia and, after a steep climb, reaches Villa a Sesta, an unspoiled village renowned for its star rated restaurants. A little further on, the fortified village of San Gusmé welcomes visitors with its timeless atmosphere. 

From here, the challenge becomes more intense. The climb to the plateau of Campi, at an altitude of 644 meters, will test your legs and your breathing. This area, chosen by the Etruscans for its breathtaking 360-degree views, is steeped in history: in the Middle Ages, the people of Siena built the fortresses of Sesta and Cetamura here, to defend themselves against the Florentines. Each bike ride to the summit is rewarded by the panoramic view. Don't miss the boundary stone marking the origin of the Ombrone River. 

The gravel road leads to the village of Rosennano and then continues to Montebenichi, a very ancient village that marks the border between Chianti and Valdarno. Here, after passing the Ambra torrent and along the Ombrone River, we come to Abbadia a Monastero, a religious building that, over time, first accommodated a convent of nuns and then the monks from the Abbey of San Salvatore.  

Returning to the asphalt road, we continue towards Castelnuovo Berardenga, passing the villa of Sestano, famous for its magnificent historic garden. You can stop for a rest at Castelnuovo, before carrying on along the road back to Pianella..