St. Augustine, FL, United States

Capital City

With a population of just 14,329, St. Augustine may seem quaint, but its colonial history and tourist-centric economy come with persistent headaches. The city's vulnerability to hurricanes and flooding is a constant concern, as evidenced by the widespread damage from Hurricane Matthew in 2016. Meanwhile, the bureaucracy of maintaining its historic buildings and infrastructure can be a drain on city resources. Yet for those drawn to the city's Spanish colonial architecture, vibrant cultural scene, and status as a winter haven for the wealthy, St. Augustine may be an ideal fit.