Cascais, Portugal

With a population of 214,124, Cascais is one of Portugal's wealthiest municipalities, boasting an expensive real estate market and high cost of living. However, the city's long history as a royal summer retreat and jet-set playground comes with a persistent bureaucratic headache. Despite the lure of stunning beaches, the region's cool, wet winters and the ever-present threat of earthquakes are reminders that Cascais is not all glitz and glamor. This charming coastal town is best suited for well-heeled retirees and remote workers who can afford its premium price tag.