We present a new method for assessing visual walkability using 360° videos and an eye-tracking in Cinematic Virtual Reality (CVR). Visual walkability refers to the walkability perceived by pedestrians through visual stimuli in the urban environment. Our method uses semantic segmentation, viewport exposure, gaze measures, and a custom walkability questionnaire, enabling comparison between scene content, participant’s viewport, and their gaze focus. The 10 videos used, including 2 calibration videos, exhibit distinct semantic characteristics, validated by segmentation analysis. Analysis of the 35 participants’ responses shows that walkability ratings at the video level correlate with several environmental parameters (e.g., road, sidewalk, sky) consistent with previous studies. However, these parameters do not have a similar influence in gaze-based visual attention analysis within the CVR setting, suggesting that CVR attention would require further work. Furthermore, our results suggest that unexpected semantic classes may also play a role in perceived walkability and should be considered exploratory pending further validation. This paves the way for further research on using CVR as an assessment tool for visual walkability and for developing methodological guidance on which visual cues are robust across measures (content/viewport).