Ipiales, Colombia

With a population of just 169,864, Ipiales may seem like a quaint Colombian city, but the reality is far from idyllic. The economy here is heavily dependent on border trade with Ecuador, which brings both opportunities and headaches - the bureaucracy around international travel and customs is a persistent hassle. And while the city's elevation of nearly 3,000 meters provides a cooler, spring-like climate year-round, the frequent rainfall on over 200 days annually can be a dampener on morale. Ipiales is best suited for those who crave an off-the-beaten-path adventure and don't mind navigating red tape and dreary weather.