The increasing pressure on urban resilience and the parallel interest in the preservation of the Historic Urban Landscape (HUL) have opened new frontiers of research that find, in the principles of the circular economy, good responses. Cities need to remake themselves from pure consumption to more resilient and circular centers, finding inspiration in their cultural and natural heritage and the history that generated it. The City of Rijeka, Croatia, one of the partners in the CLIC project (an EU-funded Horizon 2020 research project entitled “Circular models Leveraging Investments in Cultural heritage adaptive reuse”), represents an exceptional example of how to manage the change from an industrial port city to a more sustainable and citizen-oriented living space, looking at the potentials of the cultural and historical layers as opportunities for the population. The City of Rijeka, aware of such potentials, applied successfully as a European Capital of Culture 2020 (ECoC 2020), while unlikely facing the negative impacts of the COVID-19 pandemic. In Rijeka, thanks to the CLIC Heritage Innovative Partnership (HIP) program, the efforts to associate the circular economy and historic urban landscape benefit from an exceptional local awareness of the urban cultural and natural heritage, permitting the elaboration of the cultural corridor concept. By using the historical river of the city, the Rječina, as a connecting line of several heritage assets leading toward the Sea waterfront, the cultural corridor represents a space of culture creation based on continuity and proximity, where all citizens can securely reappropriate dismissed parts of the city, similar to the commons’ management practice. The cultural corridor has been imagined as a spatial implementation model that needs actions to be actuated. A set of actions was designed through the urban seeding process, tested in a workshop methodology, meant to address the HUL regeneration through an awareness-raising and cocreation approach by codesigning through situated learning, possible permanent or temporary actions, activities, assets to be replicated in the corridor and, per extension, in the entire city. This article will explain the way the cultural corridor concept and urban seeding were generated in the City of Rijeka, giving evidence of the motivations and the proposals made in parallel with the existing initiatives of the city and its cultural movements.