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Montepulciano has one square, one church outside the walls, and a climb connecting everything.

Piazza Grande, at the top of the town, is the main attraction: the Palazzo Comunale designed by Michelozzo, Palazzo Tarugi attributed to Antonio da Sangallo the Elder or Vignola, the Palazzo Contucci with a historic cellar beneath it, and the Duomo of 1594–1680 whose façade was never finished and is still bare brick.

The Madonna di San Biagio, below the walls, is the building that brings architects: designed by Antonio da Sangallo the Elder and built 1518–1545, a Greek-cross church in pale travertine standing free in open country — one of the few High Renaissance centrally planned churches ever built where it could be seen in the round.

The Corso — the main street climbing from the Porta al Prato to the square — is itself the third attraction, lined with Renaissance palace fronts and with historic wine cellars cut into the rock beneath several of them, open to visitors.

Sant'Agostino adds a Baroque church to the list, and the walls give views over the Valdichiana one way and toward the Val d'Orcia the other.