San Gimignano: A “medieval Manhattan” with a dozen stone skyscrapers.
Lodging: Skip hotels. The tourist office lists cheaper fittacamere (rental rooms).
What to Eat: The $16 meals at Osteria delle Catene, a medieval vault with modern art.
Lucca: An overlooked city of pretty churches, where locals prefer bikes to cars.
Lodging: Try family-run gems like Piccolo Hotel Puccini ($70 a room; hotelpuccini.com).
What to Eat: Cheap local delights like zuppa di farro at Da Leo, Da Giulio or Da Guido.
Montepulciano: A hill town boasting Renaissance palaces and wineries with free tastings.
Lodging: Homey hotels like Meuble Il Riccio, for $70 per double room www.ilriccio.net).
What to Eat: Try the famous pappardelle al cinghiale (with wild-boar sauce) at Via Gracchiano.
Siena: A Gothic city known for its brick palazzi, Baroque churches and friendly citizens.
Lodging: Cannon d’Oro is a bargain on the city’s main drag ($46 to $73 per room; www.svpm.it).
What to Eat: Near St. Catherine’s house, try Osteria la Chiacchera’s sinful desserts.
