On the second day of hiking we turn towards the Sienese Chianti for a panoramic itinerary of ancient towns and architectural works of great histori value. We start from Radda, an old medieval town that was the headquarters of the Lega del Chianti in the 1200s. The tradition of wine began in these hills over two thousand years ago, when the precious vineyards were already being cultivated during the Etruscans period.
After admiring the walls and the elegant palazzo del Podestà, we depart from the old mill on a dirt track that leads into a climb. We arrive at Poggio di Montemaggio and proceed on the path towards Castelvecchi. This little settlement is a centre of wine production, and today a place of hospitality; it is where millennia-old vineyards guard the tradition of Chianti Classico DOCG, and also of pinot, prosecco, grappa and olive oil.
We continue on the white roads that lead to Volpaia and Villa al Monte, and on the way find the church of the Madonna del Fossato, a little eighteenth-century chapel hidden behind the branches and encircled by cypresses. Built to house a painting of the Madonna and Child, it is a place of real mystery, should you choose to pause there. We then reach the ancient fortified hamlet of Volpaia, another historic contributor to the production of Chianti Classico.
Having visited the village, which unlike many others of its kind offers a structure both medieval and intact, we begin the climb towards the Parish Church of Santa Maria Novella, an ancient Romanesque church from the twelfth century, after which it will be easy to reach the starting point by following the white roads that flank the famous vines.