Iskenderun, Turkey

Forget the romantic vision of a historic Mediterranean port - the reality of living in Iskenderun is a bit of a headache. With a population of just 246,207, this city has been ravaged by natural disasters, including powerful earthquakes in 2023 that caused widespread damage. Bureaucracy is a persistent challenge, and the region's climate can be harsh, with the town regularly swept by a strong wind known as the 'Yarıkkaya'. While Iskenderun has a rich history dating back to Alexander the Great, these days it's more of a functional transit hub than a charming tourist destination. If you're after a laidback coastal lifestyle, you're better off looking elsewhere.