Chianti Classico Experience

From Radda in Chianti, this stage leads you through classic Chianti countryside towards San Sano. The route is not overly long, but it is varied, with steady changes in height throughout the walk. Leaving Radda in Chianti, the route first heads south with a view back towards the town before descending through the hills. After the lower section, you climb again towards the area around Giardino di Ama and Castello di Ama, where the route passes through a more open landscape with views over Chianti. From there, the trail continues close to Lecchi and follows a gentler line, with small rises and descents before the final approach.

The arrival into San Sano is straightforward, with the route easing down towards the village after the last rolling section. Your accommodation is at the end point, a good place to settle in after a varied walk through vineyards, quiet lanes and hillside tracks.

This route ends at Ponte a Bozzone, where you can call it a day and take the bus to Siena. Alternatively, you can follow route option 2, which continues all the way into Siena on foot. From San Sano, this stage leads south through quiet Chianti countryside, with rolling terrain, an early descent and a gradual finish towards the valley.

You leave San Sano on a smaller path during the first kilometres, before joining a wider track that continues south, past the entrance to the Chianti Sculpture Park. From there, you follow paths and quiet lanes through the hills, passing Vallepicciola winery before the route bends towards Villa di Geggiano and Grogno. The final kilometres lead down towards Ponte a Bozzone, where the walking route finishes close to the bus connection for Siena.

At Ponte a Bozzone, you can take the bus into Siena, with a ride of about 30 minutes. Our suggested bus stops are from GEGGIANO, Siena, in Ponte a Bozzone, to PIAZZA INDIPENDENZA, Siena. For current timetables and tickets, visit Autolinee Toscane before you travel.