The 2017 Italian port reform marked a shift from the fragmented management of individual ports to a system organized into port clusters, aligning with European objectives such as the TEN-T Core Network and the EU’s Blue Growth 2030–2050 strategy. In accordance with EU directives, Italy is now required to implement policies focused on instrumental and procedural innovation, capacity building, macro-regional cooperation, climate change mitigation, and the promotion of circular and green economy principles. In this context, port-city relations take on new significance within a systemic framework that integrates sea, ports, cities, and regions into a renewed territorial network of ecosystems. This approach entails greater flexibility in the physical and functional boundaries between ports and cities, as well as among ports within the same cluster, with particular emphasis on co-planning processes. This paper analyzes the critical issues, opportunities, and challenges arising from the reform. It aims to assess the current status of planning instruments (DPSS, PRPs) and ongoing projects in selected Italian port clusters, with the goal of outlining future scenarios that can redefine the relationship between ports, cities, and surrounding territories.