If you want to go to a place with amazing wine, I suggest Montepulciano, famous for it’s “Nobile” wine. That’s not all they have! History is everywhere. The biggest and highest of southern Tuscany's hill towns, steeply graded Montepulciano, with its medieval alleyways is a plethora of Renaissance palaces and churches.
This picture is at The Cathedral of Montepulciano, a building by Ippolito Scalza, 1592-1630. The overall structure is reminiscent of the palazzo della Signoria in Florence. The rest of the square is surrounded by several elegant buildings: In front of the church, is the ancient well "Pozzo dei Grifi e dei Leoni", dating back to 1520, it illustrates very nice renaissance work.