Port–city ecosystems face pressing challenges, such as land regeneration and environmental conservation, while striving to foster conscientious governance models among stakeholders. An innovative solution to address these issues lies in Information and Communication Technologies (ICT), acknowledged by sustainability frameworks as essential for sustainable urban development. Although ICT is regularly employed by ports for logistics and traffic management, its untapped potential for urban planning is substantial. Starting from studies conducted on port planning and management and the use of ICT as a decision support system, this research seeks to explore the feasibility of devising an innovative model to facilitate deliberative decision-making for the regeneration of port–city interaction areas. This study adopts the InterACT approach to support planning efforts by constructing an open and implementable Geographic Information System (GIS). This approach has been tested on the Port of Naples in Italy to provide the Port System Authority (AdSP) of the Central Tyrrhenian Sea with strategic guidance as part of their efforts to draft a new Port Master Plan. The initial achievements encompass the establishment of an operational database to facilitate stakeholders within the Port, in conjunction with the implementation of a deliberative decision-making process enriched by ICT. Additionally, a tool was devised to seamlessly combine visualization and spatial data integration, thus fostering engagement and collaboration between port and urban stakeholders.