[font color=\'#000000\']I suggest getting a very detailed map of the Val D'Orcia region south of Siena and wandering the back roads in the late afternoon and early evening(1) around Asciano, and (2) north and south of the road between Montepulciano and San Quirico. The landscape in that area has the classic open, rolling Tuscan hillsides with villas and cypress trees. The Chianti region, OTOH, is quite heavily wooded, and I had much less success there finding things I wanted to shoot.
Enjoy.[/font]