Walking as a daily activity has become increasingly popular in recent years. It is not only good for people’s health, but it also helps reduce the air pollution and other nuisances associated with vehicle use. As such, we have witnessed the shift in urban design towards a pedestrian-friendly city. While walkability is a broad concept consisting of many different aspects, our work focuses on only one part of it, namely “visual walk-ability”. While standard research on visual walkability tends to conduct field experiments to collect data, we present a novel method to qualify visual walkability, namely assessment in virtual reality with omnidirectional videos. We analyze the possible questions we would encounter and propose an experiment with answers for each question.