That place (Palazzzo del Capitano) looks glorious. Thanks for posting the link!

Another vote for San Quirico as a base for daytripping; it's easier to drive in and out of than either Montepulciano or Montalcino.

Have you considered Pienza? It's an easy in and out also, well-located, and a slightly bigger town with more restaurant choices.

It was Maitaitom's fabulous trip report that convinced me to stay at Palazzo del Capitano and I was not disappointed.

Logisitically, as mentioned, San Quirico.

But for a picturesque place?
Montepulciano, hands down, for me.

We were in San Quirico only for about 20 minutes, not counting the lunch we also had there. For me, it was nice, but not memorable. Much less of the old atmosphere.

To get a sense of Montepulciano, see my photos from there, at http://www.pbase.com/andrys/montepulciano
from yr 2006.

I think parking was more difficult in Montepulciano near the top.

- Andrys
http://www.andrys.com/italy.html