An exponential and badly managed use of land has led to a progressive crisis of open spaces. They become residues in-between the cities, the marginal part of the fragmented urban periphery in contact with still agricultural areas. In these territory waterways represent an important connecting element with environmental and sustainable potentialities able to create a new system with open spaces, in and outside the city, becoming opportunity to rebuild structures of meanings and to give back habitability to the open spaces of the future city. The potential of these projects is not only responding to evident ecological and biodiversity possibilities, but also to a real management of the resource that has to be in synergy with local and regional administrations. The designs dealing with open spaces along waterways have to have in themselves an effective character over a long period, on one side able to adapt to the economic potential and management of local governments, on the other able to provide a tool to indicate guidelines and objectives for the management of the territory and future cities. With this goal the research wants to investigate the territory around Milano that, as Carlo Cattaneo said, is based on an historical tradition characterized by an important domestication work conducted by man on the water, claiming, in the nineteenth century, the primacy of Lombardy in the field of hydraulic science and agriculture. Today what’s left of the domestication work are natural areas, often residual, in between a territory made of spaces strongly anthropic, where dwelling is the new protagonist and where open space for citizen public life is reduced and without quality as well as fragmentary on urban fringes. The research has set up either through didactic research, specifically through courses dealing with the topic of open spaces from the territorial scale to the specific one of single places with them equipments, either through funded research, shared with public institutions, making strong links between didactic and local policies of territorial government to think about and create a new development of the future city in relation with water (a vast topic evidenced by the work done and in progress for the Villoresi Canal that crosses whole the territory North of Milano). The studies made on the canal demonstrate how waterways become strategic places where public firm and local authorities should invest to create new urban areas and a new image of cities in relation with water, follow a trend witnessed by urban regeneration projects that especially in the last thirty years characterized and continue to characterize the cities and towns around the world.