Heraklion, Greece

Capital City

With a population of just 140,730, Heraklion is the largest city in Greece's island paradise, but don't expect an idyllic escape. The silted harbor means most shipping has shifted to the west, hampering commerce, while the city's storied history has left it with a persistent bureaucratic headache. And while the Mediterranean climate is generally mild, the occasional earthquake can wreak havoc, as the devastating 1856 quake that destroyed over 3,600 homes attests. For those who can navigate the challenges, Heraklion offers a unique blend of ancient history and modern Greek island life, but it's no tropical fantasy.