Indian cities invigorate a conspicuous imagery influenced by the pattern language evolved through their urban-morphology. Similarly, the walled cities of Jodhpur and Jaipur, though similar in context, are distinct in imageability due to difference in genesis and evolution. The paper thus focuses on wayfinding as a tool through perception of the semantics of urban elements to understand the imageability of study-area. It is based on the heuristic evaluation of imageability of the two cities, through the eyes of floating population visiting the study-area. Visual cognition and mental-map analysis of the users are preceded by spatial tasks to analyze search behaviours. Spatial perception is examined through recall tasks, which helped delineate the neighbourhood level imageability. Gaze behavior analysis through eye-tracker is performed which revalidates the findings of spatial tasks. Hence, it is established that the semantics of spatial cues have direct impact on the navigational ability and imageability of spatial environment.