Radda in Chianti
Here in the ancient capital of the Lega del Chianti, Radda in Chianti (pop. 1,650) the streets follow a medieval plan, radiating from the central piazza and its stately Palazzo del Podestà. Rebuilt in 1478, it was encrusted with coats of arms and with a 15th-century fresco Madonna, St John the Baptist and St Christopher in the atrium.
Some of Radda's medieval walls remain, but the main thing to do is soak up the medieval atmosphere of the cobbled lanes and the spectacular views over the heart of Chianti. Radda, along with Gaiole and Castellina were on Florence's front line against invasions by the perfidious Sienese.
Volpaia, 7km to the north, is another resolutely medieval village, where the convent chuch of Santa Maria al Prato has a pretty Brunelleschian cloister in a doll-sized piazza.