The limestone hill town of Montepulciano, outside Pienza, might be best known for its local red wine of the same name, a full-bodied vintage produced in the countless vineyards that surround it. You’ll certainly earn yourself a glass (or two) after making the steep hike up to Piazza Grande, whose Renaissance-era buildings are a beautiful mashup of marble, travertine, red brick, and terracotta. The Palazzo Comunale (the town hall) is one of the most striking, with a Gothic façade and central tower modeled by Medici architect Michelozzo—as well as the Fortezza, a fortress and former school turned cultural center and wine bar, where you can enjoy said glass (or two).