Following the Recognition by Unesco, since the early nineties, Habana Vieja has been undergoing an innovative urban regeneration process, based on the exploitation to culturaltourism purposes of the most important assets of the area, which assured not only the economic viability of the projects implemented but also the realization of profits. These have been systematically rechanneled to projects in favor of local communities. The revitalization Habana Vieja, however, until now has having very limited effects on the neighboring Centro Habana, which is in a state of serious decline. The article, starting from an analysis of the two cases, develops a reflection on the possibility of replicating the model "Habana Vieja" to other neighborhoods and the opportunity to frame this regeneration process in an urban strategy on a larger scale that could involve the surrounding areas, which are extremely sensitive from the urban, environmental, social and economic point of view.