Thirty years after the seminal work entitled "The Mediterranean City in Transition" by Lila Leontidou, the present contribution reformulates a narrative framework interpreting the medium-term evolution of Southern European cities and generalizes this framework to analyze other metropolitan areas with similar morphological and functional characteristics worldwide. Going beyond traditional Mediterranean discourses grounded on economic backwardness, social secularism, and demographic mix, an original interpretation of Mediterranean urbanities is proposed related to the local governance, real estate bubbles, land-use mix, and deregulation in urban expansion. Focusing on socioeconomic development processes in the Northern Mediterranean, the lost opportunity to reduce regional disparities and to give value to scenic and cultural values of the cities and the surrounding countryside are additional issues considered in this vision. Based on a narrative analysis of ecologically fragile and socially fragmented Mediterranean contexts, the pervasiveness of a structural crisis--affecting regional and country economic systems, while infiltrating the institutions, local governance systems, and the society--is finally debated as a contribution to a better understanding of complex urbanities worldwide.