The term “porosity” refers to the idea of interconnectedness between the spaces and institutions of ports, cities, and their surrounding areas. While porosity refers to the overall interconnectedness between different entities, an interface specifically refers to the point of contact and interaction between the same two entities. This paper goes beyond the idea of an interface and emphasizes a continuous network of port-related spaces and practices that shape the port cityscape. It also provides a historical perspective on the evolution of port/city boundaries. Additionally, this paper explores maps and conceptualizes port city porosity on both sea and land sides, measures, and reconsiders porosity in these regions. The thematic issue opens questions for further research such as: Can the interconnectedness between port and city areas, along with maritime pockets in the city and surrounding territory, enhance the resilience of port city activities? Does the existence of porous borders between port and city allow for easier transitions? The idea of transitions is particularly relevant in the context of the dynamic and ever-changing nature of port and city activities. As economic, social, or environmental conditions shift, there may be a need for both the port and city to adapt and evolve. The degree of porosity between them can play a role in facilitating or hindering these transitions.