Seaports (hereafter “ports”) within the European Union are facing increasingly restrictive regulation in the near future from various sources driven by climate change prevention and public opinion supporting “green” values. Ports are complex hubs for maritime transportation systems and global supply chains, as well as an integral part of critical national infrastructures. However, they are also significant individual sources of harmful emissions, and their involvement is crucial to reducing transportation-related environmental impacts. To meet future regulatory requirements, stakeholders will need to find ways to align their policies accordingly and create long-term pathways toward these ambitious targets. The empirical case study presented in this paper among European Port Cluster (EPC) stakeholders distinctly reflects the mounting importance of environmental policies and the need for further preparative measures for meeting future demands. This paper emphasizes the intensified impact of forthcoming regulation on existing business models in the EPC and contributes a foresight-based framework to approaching this issue systematically. The adoption of future-oriented regulation is a non-linear, potentially disruptive, and complex foresight process that requires each stakeholder to formulate their own strategic pathway toward a target-seeking scenario. Changing direction from the status quo toward sustainability also requires a strong commitment beyond mere regulatory compliance.