This study employed Virtual Reality (VR) and physiological sensors to study the impact of different urban elements on pedestrian wayfinding behavior and physiological responses during outdoor-to-indoor transitions in a train station context. Three urban elements — greenery, water, and leading pavement — were placed either indoors, outdoors, both, or neither, creating four experimental scenarios. In total, 35 participants completed wayfinding tasks across all four scenarios. Behavioral, physiological, and eye-tracking data were collected and analyzed. The results revealed that outside-only placement of urban elements was associated with the worst wayfinding performance across all metrics, performing worse than even the control condition with no urban elements. Eye-tracking analysis demonstrated that outside-only placement of urban elements actively distracted participants from the indoor navigation path. Inside-only placement supported the most efficient navigation in terms of travel time, while the scenario with elements in both locations produced the most focused gaze behavior and the highest subjective comfort ratings. These findings highlight that the placement location of urban elements is more critical than their mere presence for supporting outdoor-to-indoor wayfinding, with important implications for human-centered design in transport hubs.