Rüdesheim am Rhein, Germany

With a population of just 10,180, Rüdesheim am Rhein is a quaint German wine town, but don't let its picturesque charm fool you. The bureaucratic headaches of navigating its five distinct quarters and patchwork of local regulations are a persistent hassle. And while the Rhine Gorge landscape is celebrated in romantic lore, the climate can be bitterly cold in winter. Still, Rüdesheim's 1,000-year history of viticulture and status as a major tourist draw make it an appealing option for oenophiles and those seeking a quiet, pastoral lifestyle.