Modernity is characterized by governments have sought to govern the urban condition through direct regulatory interventions such as those prescribed in the Athens Charter and adopted worldwide for many decades. However, the governance tools for urban design have demonstrated not to be able to elaborate new urban models able to represent the multiplicity of the existing city. This lack of planning-design consequentiality is well represented in the Mediterranean port-cities because of the co-existence of different and even contradictory issues, as within the Mediterranean port-cities conflicting dualities can be found: on the one hand there is the relationship between the city and its heritage, while on the other there is the relationship between the new role the historic port and the modern, commercial, harbor. These dualities collaborate in the definition of the urban reality of the Mediterranean port-cities, as well as in the description of their contemporary condition, where all these issues are simultaneously present. Thus, the contemporary image of the port-city has to deal with both the past (historical heritage) and the future (the role of the port infrastructure), as well as with the transformation of the «reality» of the existing environment into the «hyper-reality» of hyper-tourism. Thus, the issue of authenticity is a key issue that regards the image the city has of itself as well as the image it wants to promote in order to participate to the global urban competition.