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.

Pienza was once a regular medieval village called Corsignano. That is, until one of its sons became Pope Pius II and decided to transform his hometown. He hired architect Bernardo Rossellino and rebuilt the area based on Renaissance ideals of symmetry, order, and harmony. The result? A site that feels intentional. The central square, Piazza Pio II, is flanked by a cathedral, a papal palace, and a town hall, all arranged just so. Moreover, Pienza is known for pecorino cheese—sheep's milk, aged in interesting ways. And once a year, the whole town turns into a cheese arena for Fiera del Cacio, a festival featuring Cacio al Fuso—a game where people roll wheels of cheese at a target.