Holetown, Barbados

With a population of just 1595, Holetown is a sleepy Caribbean town that offers little in the way of bustling city life. The island's oldest church, erected in 1628, provides a glimpse into the town's colonial past, but the persistent bureaucracy and red tape that comes with living in a former British protectorate is a headache for many. While Holetown celebrates an annual festival commemorating the first English settlement, the reality is that this tiny enclave offers little beyond a scenic coastal setting for those seeking an island escape.