This text discusses some practices and theories related to urban planning and architectural design in a UNESCO listed city, promoting a shared approach on the theme of Urban regeneration in Historical contexts. The practices and theories derive from researches and didactic experiences that I have developed with other professors and students in Havana, Cuba. The first one with CUJAE Instituto Superior Politécnico José Antonio Echeverrìa was the international cooperation program PatrIndArch on Water Heritage (2013-15), in which CUJAE Cuba, University of Alicante Spain, University of Padova and University of Ferrara were involved. From this pedagogical experience came the opportunity to program an international Seminar dedicated to “Water, Architecture and Landscape in Europe”, held in November 2014 in Instituto Universitario del Agua y de las Ciencias Ambientales, Universidad de Alicante, where I participated with professors and researchers from the Universities of Ferrara, Padova, Alicante, Coimbra, Bucarest, Valenciennes et Hainaut-Cambrésis, with proceedings published in 2015. This text is mainly derived from the PRIA research program “URB_HE Urban Heritage Conservation as vector of social equity”, in which I participated (2015-17), and which was financed as an “Interdisciplinary research project” by the University of Ferrara under a call for proposals dedicated to defining new international fields of research. This research and pedagogical activity wwas related to the concepts of rehabilitation, regeneration, heritage conservation, which were considered like “moving concepts”. The emblem of this dynamic is the evolution of the concept of heritage: from tangible to intangible, from monuments to cultural landscape. Havana and its territory represent a privileged case study from which to observe not only influences of European and North American culture on the Global South cities, but also original hybridizations deriving from the intertwining of different practices related to urban planning and architectural design in UNESCO cities.