This paper is based on the research project-"LONGEVICITY"-carried out in the Metropolitan Area of Milan, which looks at the cities of the future as highly populated by long-living active people and innovative technological facilities. The project is conducted by a multidisciplinary research approach to study how to support social inclusion of elderlies' living in urban environments by enhancing their active walking. The whole process will engage participants (senior citizens) and stakeholders in a human-centred design approach. In this paper we will present the results from the preliminary research activities carried out: case studies and territorial observations. The first activity was oriented to investigate and select innovative solutions to enhance the mobility of elderly pedestrians and to improve their (social) lives. The second one helped us in better framing the design context of action and assessing at, a microscopic level, the degree of walkability of specific territorial areas.