Central Tuscany’s cities supply textbook examples of Italian hill towns. In particular, the Roman settlements of Montalcino and Montepulciano. Both grew into medieval centers that today produce some of Italy’s most important wines. Brunello di Montalcino, a powerful, cellar-worthy red Americans have developed a taste for, and the humbler Vino Nobile di Montepulciano, a great value from the right producer for which Americans should develop a taste. In between the two sits the jewel box village of Pienza, notable for high-quality pecorino cheese, charming restaurants with vista views, and the Renaissance achievement of proportion and city planning.