In recent years waterfronts have progressively become the focus of local administrations, consultancy agencies, and private developers concerned with public health, city branding, and real estate development. Subsequently, they turned into central stages in which cities and societies can be represented, contested, and inverted. However, many questions remain unanswered concerning their capability to function as counter-spaces in the fast-changing dynamics of citizens’ encounters and recreation in global cities. This paper employs mixed methods to examine the context-dependent association between space and behaviours. The comparative analysis of four waterfront parks in Venice, Shenzhen, Hong Kong, and New York sheds light on heterotopic sites’ production and use. Two models emerged: transient spaces of compensation and time-accumulating spaces of illusion. Beyond the novel research design, the significance of this study lies in validating Foucauldian-Lefebvrian heterotopology as an authoritative analytical paradigm for a critical interpretation of the urban.