Physical inactivity is a risk factor for chronic diseases and ischemic cardiomyopathy, which is the leading cause of death in Bogota, Colombia. Cycling is a sustainable strategy to increase levels of physical activity, especially for college students; however, fewer women than men engage in this activity due to gender roles, creating an avoidable inequity. The aim of this study was to understand the socio-cultural significance perceived by a group of medical students in women’s use of bicycles as a mode of transportation in Bogotá. Qualitative research based on grounded theory was conducted. Sixteen students participated in three focus groups and four interviews from February to April 2018. We found that the meaning of the cycling experience resulted from identity construction. The cycling experience involved both sociodemographic conditions and a transitional gender model with competing notions from a traditional and a contemporary model. The traditional view on bicycling emphasised the insecurity of women based on underestimation of their capacities. This model generated perceived vulnerability and affected undermined women’s self-efficacy. In the contemporary model, bicycle use facilitated well-being and served as an efficient means to commute. To increase female students’ participation in urban cycling, it is essential to encourage the construction of self-efficacy. It is also necessary to improve safety in public spaces and facilitate bicycles’ convenience of use. This actions could support sustainable transportation, gender equity and reduction of health risks related to physical inactivity.