Castles, vineyards, walled cities and a fierce medieval rivalry that lingers today—we're out for an adventure in the Italian hill towns. Our base is dramatic Siena, home of the intensely competitive Palio horse race. From Siena we explore the multi-towered town of San Gimignano, watch grapes being harvested at a winery and drop in on the cheese festival in Pienza. Then south to Rudy's secret pick—the haunting hill towns of Pitigliano and Sovana. In Umbria we discover Etruscan tombs, visit the home of St. Francis of Assisi and pick up some pottery in quaint Gubbio.