The circular economy (CE) brings many opportunities, but also many challenges for ports, cities, and their hinterland. The goal of this paper is twofold. First, we embrace the inherent uncertainty of the spatial impact of the CE on ports and cities. We employ scenario methodology to guide us in steering this uncertainty by developing four scenarios. To explore the complexity of these four scenarios, we focus on the Dutch province of South-Holland. This region hosts the port of Rotterdam, the largest port in Europe, and its direct hinterland consists of a dense urbanised region. As such, the four scenarios cannot only shed a light on the future of the port, but also how its relations with its direct urbanized hinterland can potentially change. In two scenarios deglobalisation occurs. The consequences are, on the one hand, that the port's focus changes more to its direct hinterland instead of a global oriented focus. On the other hand, the existing water bound industrial areas in, or nearby cities increase in importance, in contrast to the contemporary pressure to redevelop these into waterfront residential and commercial areas. In other words, port and city/region grow towards each other. The second goal of the paper is to dive into the specific consequences of these scenarios for day-to-day planning practices. By combining micro-economic and AIS shipping data, we discovered the most important terminals and industrial areas for the transition towards a CE in port, city, and hinterland.