Ponta Delgada, Portugal

Capital City

With a population of just 68,809, Ponta Delgada may seem like a sleepy island town, but the reality is anything but. Bureaucracy is a persistent headache, with the city serving as the administrative capital of the Azores region. And safety has deteriorated sharply in recent years, with a 32.6% share of the archipelago's 3,188 criminal cases in 2023. Still, the mild Mediterranean climate and stunning volcanic landscapes make Ponta Delgada an appealing option for those seeking an island escape - as long as they're prepared to navigate the local red tape.