We're flying into (and out of) Bologna at the end of October and returning to the U.S. on November 19th (so about 19 days in country). We've got 3 nights booked in Bologna, which we visited before and loved years ago, but would like to spend the rest of our time in Umbria and Tuscany. Assisi is the only touristy "must" on our wish list but otherwise we'd prefer to be in smaller towns. We're hard-core food and wine folks and especially interested in experiencing the various manifestations of the sangiovese grape in its more accessible and affordable manifestations (i.e. Chianti, Rosso de Montalcino, Vino Nobile but skipping Brunello and anything else that needs 10 years of aging to be worth drinking).
Spello and Montefalco in Umbria seem appealing, as does spending time in Tuscany on some part of the Chianti route or perhaps using Siena as a base for trips? We were initially planning on just using trains and buses but will rent a car if need be. I've driven the tiny "D" roads in France extensively and have no problem with tiny cars with a stick shift but know that leisurely lunches with wine and driving the vineyard roads are an ill-advised mix.
Any thoughts appreciated!