I highly recommend Montalcino as a great place to stay - extremely friendly town, not too large, good restaurants and many wine bars where you can taste local Brunello. We were there in August (TOO HOT!!) and stayed at a lovely place that is a converted olive factory - called Vecchia Oliviera, right as you enter the town. We enjoyed visiting Pienza, Montepulciano, which are only short drives from Montalcino. Also the Abbazia di San Antimo is nice to visit. If you enjoy walking, get the book "Walking and Eating in Tuscany" (Amazon carries it) - we did one of their walks and thoroughly enjoyed being in the countryside. (I disagree with the person who favored San Gimignano - it is thoroughly touristy, a Renaissance Disneyland. Montalcino is much more real)