Sanremo, Italy

With a population of 65,000, Sanremo may seem quaint, but its bureaucracy is a persistent headache. The city's Mediterranean climate and tourist appeal come at a price - high costs and heavy traffic. While it's a hub for cultural events like the annual Sanremo Music Festival, the reality is Sanremo caters more to the wealthy and privileged than the average expat. Unless you're a fan of gambling or have a deep appreciation for flowers, this resort town on the Italian Riviera may not be the best fit.