This is the land of one-hill views, meaning the hilly terrain lets you see only the hill before you. Wonderful for gazing close up at vineyards, ruins, and castles. The best base is Greve, close to Florence. Wind south to Panzano, then through Castellina towards Poggibonsi. Go slow, this is beautiful especially in the autumn light. Do have lunch at Alcide, a non-descript hotel and restaurant that makes a wonderful Livornese fish soup called cacciuco. From Poggibonsi take a back road south to Colle di Val d’Elsa then on to Monteriggioni. Pass Siena (save it for another day because there is way too much to see) then take a back road to Castelnuovo Berardenga, north to Gaiole, then Radda, then back to Greve.