What are the roads like between Urbino to Montpulchiano? Are they paved?
Are they really windy mountain roads?
I've driven Urbino to Assisi and Assisi to Montepulciano which is essentially the same route, and the roads were perfectly fine. In fact, some were quite good. There were some hills but I don't recall any winding mountain roads. And yes, roads in Italy are paved.