Understanding the determinants of cycling and thus creating optimal cycling conditions is still a challenge. The current study addresses this challenge by providing in-depth exploration of attributes of bicycle infrastructure, traffic volume, gradients, urbanisation degrees in stimulating cycling for various population categories. Participants had to cycle in a simulated VR environment mirroring the streetscape of a real Dutch city. The cognitive (e.g., safety perception) and affective (e.g., enjoyment, attractiveness) response was measured, real time. The results suggest that various attributes impact the cognitive and affective components to different extents. In particular, bicycle path presence and intersection absence had a positive impact on safety perception. Greenness of the environment contributed for lifting the attractiveness of the cycling experience. Hight car traffic had a negative impact on the way safety, enjoyment and attractiveness of cycling was perceived. Current outcomes should be implemented in creating bicycle infrastructure that appropriately meets the demand for attractive cycling experience that is safe and enjoyable for all.