Montepulciano is a classic medieval town. The highlights are the church (Duomo) with the central squares, the very steeply sloping passageways and the renaissance buildings. The wine in this area is the most famous in Tuscany, Vino Nobile.
In order to get there, leave Rome and take the A1 in the direction of Firenze. Continue some 170km and take the exit marked Chiusi-Chianciano Terme towards Chiusi. Then take the 146 and follow the signs for Montepulciano. It is a 2 hour trip and costs around 8-9€ in motorway toll charges (pay by credit card because the cash booths are usually crowded. "Black" Money flies in Italy...).
