Trinidad, Uruguay

Capital City

This tiny city of 22,893 in southern Uruguay is hardly the paradise some expat dreamers may envision. The bureaucracy is a persistent headache, with the city's name and status changing no less than three times over the years. And while the nearby nature reserve offers some respite, the climate can be harsh, with the city sitting at an elevation of 134 meters above sea level.

For those willing to navigate the red tape and weather the challenges, Trinidad may hold some appeal. The city has a long history, having been founded by a Uruguayan independence leader in 1805. It's also the largest in its department, offering more amenities than the surrounding rural areas. But overall, this sleepy, isolated outpost is best suited for a certain breed of hardy pioneer, not the faint of heart.