One significant and simultaneously interesting problem in urban mobility has to do with the study of shared spaces where various categories of users coexist and act together. This paper aims to examine the behavior and preferences of pedestrians and cyclists, who both coexist in a shared space infrastructure along the seafront (which has a length of around 4.0 km) of the city of Thessaloniki, Greece. Furthermore, the problems caused by the coexistence, such as at the locations where there are pedestrian crossings on the bicycle lane, are recorded and evaluated. Traffic calming measures aimed at improving the existing situation in terms of safety and comfort for both pedestrians and cyclists are also explored. Data were collected through a web-based questionnaire survey, which was distributed via email to students and employees of Aristotle University of Thessaloniki. A total of 1194 questionnaires were collected in the framework of the survey during the year 2021, including responses from both pedestrians and cyclists. The questionnaires were analyzed through the use of descriptive and inferential statistics; the latter method suggested several significant differences in how each group of users (pedestrians or cyclists) perceived their behavior compared with the other. Latent variable and path models were estimated to investigate the behavior and attitude of users towards the crossings, examined as a function of their perception towards the other group; perception about the benefits of the infrastructure; preference for additional interventions; and overall opinion about the quality of the shared space area. The results suggest that forms of aggressive behavior, preference towards using the crossings, and the perceived safety are affected by the aforementioned factors. The results of this study can inform decision takers and decision makers in the area of land use regarding policy recommendations for facilitating interactions between pedestrians and cyclists in shared spaces.