In a general urban planning context, in which sustainable active mobility progressively takes up increasing attention, studies of cyclists’ attitudes and behaviors represent a relevant step to help any enhancing measures for urban cycling. Among different categories, university student cyclists represent a still unidentified class, despite the relevant impacts in terms of mass and variability of attitudes in urban areas. The novelty of this paper is to propose an innovative overview on the specific category of university student cyclists. The integrated methodology, based on direct observation through GPS detection, GIS processing, and qualitative survey, permits the evaluation of some interesting issues related to students’ propensity to cycling and their mobility patterns. The approach finds relevance in speed, frequency of movements, routing, and related infrastructure preferences. The methodology has been applied to a sample of more than 300 students of the University of Bologna who were allowed an original university-designed bicycle from February 2021 to June 2021. The analysis was applied in the Bologna urban area and allowed the evaluation of students’ preferences of using existing cycle paths, when available, the limited relevance of speed factors, the main distribution of commuter journeys concentrated in the main avenues directed to city center, and other behaviors.