Cycling constitutes a clean, healthy, and low-cost mode of transport. Therefore, the promotion of cycling is currently one of the main goals of administrations around the word. Former studies have shown that safety perception plays a fundamental role in the acceptance of bikes as a habitual mode of transport. In this context, this research aims to determine which variables and actions can give rise to this feeling of safety and, therefore, collaborate in the modal shift towards a more sustainable mobility. For this purpose, different strategies have been developed in two different contexts, Helsinki and Barcelona, using two different methodologies, namely expert interviews and analysis of survey data. Particularly, the methodology of analysis used includes descriptive statistics and path analysis. Results point out that safety perception highly depends on trip purpose, as significant differences are observed for daily users compared to those who cycle for sport reasons. Demographic characteristics (age, gender, etc.) and use patterns are also associated with different perceptions of safety and different behaviors. However, for any cyclist, the quality of the available infrastructure significantly influences his/her safety perception. Thus, the provision of good quality and well-structured cycling infrastructure is the most important initiative to promote cycling.