Town of Pienza in Tuscany, Italy

A taste of Pienza

Some towns evolve slowly over centuries. Pienza? It received a full rebrand in the 1400s from a pope who wanted to prove a point—and maybe show off a little. This tiny Italian town is perched above the Val d'Orcia, surrounded by rolling hills that look exactly like you think Tuscany should: cypress trees, winding dirt roads, the occasional sheep. It's peaceful. And then you step inside the town walls, and it gets clever.