San Andrés, Colombia

With a population of 63,692, San Andrés boasts a thriving tourist economy, but the reality is that bureaucracy is a persistent headache for residents. The island's tropical monsoon climate brings high humidity and unpredictable storms, while the influx of mainland Colombians has strained resources and local culture. Despite its picturesque beaches and duty-free status, San Andrés may not be the idyllic island escape that some expect - it's best suited for those drawn to its Caribbean charm who can navigate its challenges.