Pienza is the ideal city that one man built for himself, and it is as extraordinary as that sounds. It began as a village called Corsignano, the birthplace of Enea Silvio Piccolomini, who rose to become Pope Pius II. When he returned in 1459 as pope, he decided to turn his home town into a model Renaissance city, and he hired the architect Bernardo Rossellino to do it. In only a few years, the place was rebuilt around a perfect trapezoid piazza, with a cathedral, a papal palace and a town hall, all in the new classical style. The pope died in 1464 and the plan was never completed, which is why Pienza is still so small and so perfect, like a stage set frozen in time. It was named a UNESCO World Heritage Site in 1996.
The setting is the Val d'Orcia, a landscape of rolling hills, cypress-lined drives and isolated farmhouses that has become one of the most photographed in Italy. The clay soils create gentle, bare ridges, and in spring the fields are bright green, in summer golden, and in winter often wrapped in mist. The town stands on a ridge above it all, with a terrace behind the cathedral that gives views across the valley to Monte Amiata. It is the sort of scene that makes you want to stop on every corner.
Riding here is a pleasure. The roads are narrow, curving and well maintained, passing between fields and vineyards at an easy pace, and the corners are mostly gentle. Traffic can be heavy in summer, with coaches and rental cars, so the best times are early morning and late afternoon, when the light is golden. The town centre is restricted to traffic, and you will need to leave the bike outside the walls and walk in.
Pienza is also famous for its cheese. Pecorino di Pienza, made from sheep's milk and aged in various ways, is sold in dozens of shops along the main street, and the sampling is generous. The town has plenty of restaurants and bakeries, and a lunch of pasta, pecorino and a glass of Vino Nobile from nearby Montepulciano is as good as it gets.
For fuel, the small town of San Quirico d'Orcia, about six kilometres to the west, is the nearest option, and Chianciano Terme, about twelve kilometres, has more choice. Fill up before climbing into the hills, as pumps in the countryside are few.
Take time to wander the narrow lane called Via dell'Amore, a path around the walls with the view over the valley. It is worth the ten minutes even if the name makes you smile.