Take a small detour off of Via Chiantigiana onto Statale SR429 and find two little towns that have retained their medieval charm: Radda in Chianti and Gaiole in Chianti.
Gaiole in Chianti, which also retains its medieval wall, is just a bit further down the road from Radda. It started as a little village in the 1000s and later turned into a very important merchant city closer to 1215 when the surrounding towns began using it and its convenient locality and large piazza as the perfect central point to create an important market. Different castles, like Castello di Meleto and Castello di Vertine, as well as churches like the Pieve di Spaltenna still stand, keeping the city alive in its medieval splendor.