By analyzing a series of territorial paradigms proposed by theorists, critics, and designers, this chapter offers a critical overview of the recent transition from metropolitanist to regionalist perspectives over today’s expanded dwelling space in the global debate. The analysis tackles metropolitanist models related to Manhattanism and neo-nomadism with reference to their avant-garde and radical parentages. The text critically investigates models derivative of metropolitanism, such as landscape urbanism, urban age, and post-metropolis, along with models that present themselves as alternative, such as sub-urbanism and mega-regionalism. The text confronts metropolitanist models and their filiations with the principles of the disciplinary refoundation based on the idea of urban space, such as those of Tendenza, and with the traditional constructs of territory and landscape, such as those of the Italian landscape and the trio of natures, which they propose to subvert. The theoretical elaborations of landscape urbanism are then confronted with their geophilosophical references. The text proceeds to observe the process of expansion of the idea of city over the geographic scale. A novel form of expanded urbanity, surfacing from the analysis, finally suggests the opportunity to identify a set of novel attributes relative to the citizenship of the contemporary built/natural continuum. The conclusions identify the idea of a territorial mythology, unawares and fragmentarily building up in the contemporary continuum, as a possible field of future research and design work.