From Radda in Chianti to Castellina in Chianti and back

A looped itinerary to discover the Sienese territory between the villages of Radda in Chianti and Castellina in Chianti, until reaching the Chianti Fiorentino. This short route of 23.6 miles or 38 kilometers can be quite intense due to the 2162-feet (659-meter) gain in elevation. 

Start out from Radda in Chianti and follow the SR222 Chiantigiana road to Castellina in Chianti, skimming past the Poggio alla Croce Archaeological Park. In Castellina, you can catch your breath, taking the opportunity to visit the historic center, with the charming Via delle Volte and the splendid Rocca, housing the Archaeological Museum in the Siena Chianti within. Climbing to the top of the Rocca will also provide unparalleled views of the surrounding area.

From Castellina in Chianti, head up the SP76 road to 2047 feet (624 meters) then descend to the viewpoint at the Poggio di Ricavo junction from where, through dense woods, you reach Nittardi. From here, a nice traffic-free paved road allows you to reach the Pesa River before heading in the direction of Panzano in Chianti. 

At Fontodi, take the SR222 Chiantigiana road once more to reach Lucarelli, skirting the Pesa River. From here, the last stretch takes you back to Radda in Chianti, climbing up the “Valle dell’Oro” (“Valley of Gold”) in Pesa, so named because of the presence of gold diggers in the 1880s.