A tiny fortified village four kilometres east of Pienza, perched on a hill that gives one of the iconic views over the cypress-lined road below. Monticchiello is administratively a frazione of Pienza but completely different in feel — a single curving street inside intact medieval walls, half a dozen buildings, and very few tourists outside high summer.
The fourteenth-century parish church of Saints Leonard and Christopher has a fresco cycle attributed to Pietro Lorenzetti and his workshop. A couple of decent restaurants overlook the valley; book ahead in summer. The walk down from the village to the famous cypresses at the bottom of the hill takes twenty minutes.