Transport and mobility are crucial factors in the process of adaptation of contemporary urban areas to the challenge of sustainable development. In this perspective, however, cities need to perform a more effective integration between a wide range of different policies and planning practices. Together with a more effective integration between transport policy and land-use planning, for instance, cities could take growing advantage by organisational factors, as well as the spreading of new technologies and the related processes of social innovation. Through the description of several project and planning initiatives taking place in Palermo, the fifth Italian city, this paper attempts to explore the potential sinergies between the “hard factors” of mobility—in this case given by the huge programme of infrastructure redevelopment under realisation in the city—with some other dimensions, such as urban regeneration processes, governance and community-led processes of innovation.