The human factor plays an important role in the successful design of infrastructure to support sustainable mobility. By engaging users early in the design process, information can be obtained before physical environments are built, making designed spaces more attractive and safer for users. This study presents the collected data of a virtual reality (VR) application in which user perception has been evaluated within an urban redevelopment context. The area under consideration is the Canal of the Port of Rimini (Italy), a degraded area not connected to the city center. The redevelopment of degraded urban areas is the first step towards achieving the sustainability aims set out in the Sustainable Development Goals. Prior to this work, evaluation methods were developed in the decision-making process, considering different social, economic, and environmental aspects in order to obtain a priority scale of interventions for urban regeneration. Architectural solutions were proposed to represent targeted and specific interventions that are designed precisely for the context to which they are dedicated in order to make the Canal Port area a continuum with its urban context and to improve its perception by tourists and inhabitants. To assess these proposed infrastructure modifications, two models of VR were created, one relevant to the current condition and one representing the future condition after redevelopment of the area. Virtual visits to the Canal of the Port of Rimini were created under two scenarios, namely, the current situation and the future situation after redevelopment of the infrastructure. Then, human participants were involved through two different questionnaires. The first allowed participants validate the VR model created by comparing it with the real context, while the second served to evaluate the perceptions of users by comparing the two VR models of the canal before and after the intervention. The results of this empirical research highlight the benefits of engaging users early in the design process and improving the user experience before implementing renovation of the infrastructure.