This paper analyses more than 200 ‘car-free’ city initiatives, from 95 different cities around the world, aimed at refocusing car-based transport and urban planning towards sustainable transport and as a strategy to create more liveable places. The initiatives were analyzed and classified in terms of their rationale or objective, scale and level of implementation. Six key underlying objectives were identified for the initiatives: i) reduce car use attractiveness by making it more inconvenient and costly, ii) increase the attractiveness of sustainable modes and integrated transport systems by making them more convenient, iii) revive social functionality of streets, iv) reduce environmental impacts of transport, v) promote sustainable housing developments and vi) rationalize freight operation. This research illustrates how transport supply is strongly shaped by policies and how transport demand is driven by people’s aspirations but also as a response to the context set by the provided transport supply. The analyzed initiatives highlight the need for multidimensional sustainable transport strategies to overcome car-dependency and to achieve wider sustainability goals. The research underscores the role that technology has in enabling both changes in supply through new types of mobility, but also changes in demand, especially as a platform for social movements to organize and create the critical mass that enables cultural shift. The studied initiatives make evident that in the context of a technology intensive future mobility, aspects like electric cars, or even automated cars, if conceived in the same socio-technical system as current cars, contribute only marginally to liveability in cities.