San Cristóbal de La Laguna, Spain

At 161,108 residents, San Cristóbal de La Laguna is a sizable city, but one that still grapples with the bureaucratic headaches common across the Canary Islands. The city's historic center may be a UNESCO World Heritage site, but the government's transfer of the capital to Santa Cruz de Tenerife in 1723 has left La Laguna with a declining population and economy in the centuries since. While the city's Mediterranean climate provides respite from the arid conditions found elsewhere in the archipelago, it also brings higher humidity and less sunshine compared to its neighbors. For those seeking the cultural charms of a colonial-era Spanish city, La Laguna may hold appeal, but the persistent administrative challenges make it a poor choice for those seeking an easy relocation.