Eastbourne, United Kingdom

The Eastbourne Open is a major tennis tournament, but that's about the only highlight for this coastal city in the UK. With 11 singles titles, Martina Navratilova's dominance shows how little has changed here over the decades. Bureaucracy is a persistent headache, as the event's sponsorship and location have shuffled around since 2009. While the grass courts provide a "warm-up" for Wimbledon, the lack of excitement and amenities makes Eastbourne a tough sell for most expats. This sleepy seaside town is best suited for retirees seeking a quiet, unchanging pace of life.