The contemporary city, with its processes of upscaling and rapid mutation, produces, together with great possibilities also great contradictions and risks that question the very idea of a city. Emerging are new forms of spatial inequalities and injustice, new problems of metabolism related with the management of in-out flows (such as water, energy, goods, people) and their carrying structures. These processes are related resulting in a more difficult and uncertain condition. This condition challenges the role of designer and design practice as a specific means of knowledge production. Does this condition, “between chaos and potentials” (Koolhaas 2014) make the project of the contemporary city and territory possible? What are the constitutive features of a project that is able to absorb these contradictions and create new conditions of possibilities in the framework of a meaningful order? The praxis and reflection of different agents are today reframing the fields of urbanism and landscape architecture; new concepts and principles replace others at the centre of these disciplines and guide the construction of new discursive as well as spatial forms. Landscape Urbanism is one of the successful neologisms. In the notion of Landscape Urbanism, positions converge that have in common the retrieval of concepts such as memory, social utility and ecology. A depth that leads to new forms of description and prefiguration. As cultural construct, landscape is made and remade. The interpretation of landscapes imply - using the terms of Umberto Eco - the distinction between the “intentionality of the author”, that is what the author wants to communicate; the intentionality of the “reader”, that is what the reader interpret and use. And the “intentionality of the work itself”, that is what - independently from the intentionality of the author – the constructed landscape suggests remaining open to new interpretations.