Originally Posted by andrey_gta
Can you share the locations of these roads?
Heading south out of Firenze(Florence), use TomTom to navigate to Falciani city center. Once you clear Firenze city limits, navigate to latitude 43.0991333 by longitude 11.3448167 with the settings changed to Winding Roads Maximum. Keep those settings and nav to Montalcino and then Orvieto in that order.
This is the general idea, but without the amazing TomTom winding roads feature: