São Vicente, Brazil

São Vicente may be the "cradle of American democracy," but it's hardly a utopia for expats. With a population of just 268,618, this coastal municipality is more bedroom community than thriving metropolis. The bureaucracy is a persistent headache, and the narrow island geography means housing options are limited. While the historic tourism and beaches offer some appeal, the reality is this isn't the place for those seeking an easy, seamless transition abroad. São Vicente is best suited for hardy souls willing to navigate its quirks.