Portmore, Jamaica

With a population of 166,845, Portmore is one of the largest urban areas in Jamaica, but it's no paradise. This commuter town was hastily built to alleviate Kingston's housing crisis, and the results are mixed. The canal system may prevent flooding, but the bureaucracy is a persistent headache. And while Portmore isn't a top tourist draw, it does offer some entertainment options like beaches and horse racing. Overall, this city is best suited for practical-minded Jamaicans looking for affordable housing, not sun-seeking expats.