We (six adults) just returned from three weeks in Italy, Spain and London. Our Italian stint was October 19-26. We focused our Italian vacation on the Medieval Tuscan Hill Towns between Siena and Florence. We rented Villa Fiorenzia in Radicondoli, Italy...about 45 minutes south of Sienna and 45 minutes west of Florence. It was a perfect tiny hamlet with a Medieval tower from which to start and end our touring each day. The towns listed by the 2012 Rick Steve's book are good, but if you are up for great fun, we recommend discovering all your own. All of these towns were involved in the wars between Sienna and Florence. At one point, or for some still, they were walled cities with family built towers sitting on hill tops. As you drive through the countryside you just see them sitting up there as you draw closer and closer to them. And, right smack in the middle of it is the Chianti Classico region with some of the best wines, even for us big, bad, bordeaux style cabarnet drinking Washingtonians. We literally dropped in on Casa Solaan ancient family estate that is a Chianti Classico wine producer...without an appointment and in a shoulder season, we were led on an impressive tour of the grounds and vineyards and got literally hands on viticultural lessons then were taken into a private tasting of their entire current release complete with advice on how to taste and house made olive oil, fresh bread and cheese and salumi. The experience will be a memory for a lifetime.