Bertinoro, Italy

This hilltop town of 11,026 residents isn't exactly a glamorous expat haven. The medieval castle and historic architecture are quaint, but the bureaucratic headaches of Italy's rural regions loom large. Navigating the local government and services can be a persistent challenge. Still, the annual "Hospitality Festival" suggests a warm community spirit, and the nearby university campus provides an intellectual draw. For those seeking a taste of traditional Emilia-Romagna living, Bertinoro may be worth a look, but it's no idyllic escape.