We stayed at a castle 15 minutes from Cortona called Montegualandro. We asked the owner what winery within 100 miles would he reccomend? He said without hesitation "Redi in Montepulciano". He said it had a small sign and was hard to find.
From the front door you descend into a late 16th century structure, beautiful stone arches that spring from the rock as you descend, until you end up at a lower entrance, and an elegantly dressed young woman with bottles to taste. We were alone the whole time.
Panasonic DMC-L1 hand held
Comments appreciated, thanks for looking.