Montepulciano is a Tuscan hilltop gem. All of its streets are steep, so the trek up its winding alleyways can be hard work, but their medieval beauty and the excellent views to be had all around town make it all thoroughly worthwhile. Montepulciano is also known for its wines. The town is touristy, but it isn’t quite overwhelmed to the degree as some of the other towns closer to Florence. The Piazza Grande is the town’s finest, and is surrounded by fine sights such as the Palazzo Comunale. You can climb the clock tower of the Palazzo Comunale, daily 10am-6pm. Entry fee applies. The Duomo had its interior completed before the city ran out of money, leaving the facade undone. Daily 9am-1pm, 3pm-7pm.