In the context of sustainability, ports often emerge as points of contention involving stakeholders from the maritime industry, local government, and communities. The interaction between ports and cities reveals that effective communication and the cultivation of maritime culture can serve as a potent combination for the transmission of information between the port and the city. This implies that the successful development of a port can be achieved by establishing a well-functioning communication channel for the exchange of knowledge, actions, experiences, and cultural values. The research idea postulates that the cultural component can serve as an additional dimension within the frameworks of sustainable development and resilience enhancement research, specifically within the domain of port organizational resilience and sustainable development. Notably, substantial attention is directed towards small and medium-sized ports, as these entities are particularly susceptible to the influence of the port on the surrounding social communities, owing to the intricate interconnections among culture, heritage, and environmental conditions. The subject of this study centres on the cultural interaction between ports and cities. The research goal is to explore the impact of port-city cultural interactions on the sustainable development of medium-sized port cities and their associated coastal regions. To this end, the research is guided by specific objectives, which include elucidating the concept of port-city interaction and situating this interaction within the broader context of sustainable development in coastal regions. Furthermore, the study aims to delineate the cultural component within the framework of port-city interaction and, subsequently, to propose potential trajectories for the development of port-city cultural interactions that could enhance the sustainability of coastal regions. The research methodology employed in this study adheres to the methodological principles of a theoretical approach. This approach encompasses the systematic exploration of concepts, theories, and existing knowledge within the chosen domain, thereby providing a robust foundation for the investigation. The main results found out that, the integration of culture into port-city interaction is vital for fostering sustainable development and resilience in coastal regions. As a dynamic and multifaceted component, culture influences communication, shapes organizational ecosystems, and contributes to the achievement of SDGs. Also, as it was suggested the port-city interaction's evolution trajectories not only enhance the socio-environmental fabric of port-city dynamics but also offer a roadmap for fostering enduring sustainability and excellence in coastal regions.