Previous work is reviewed and an experiment described to examine the spatial and strategic cognitive factors impacting on human orientation in the ‘drop-off’ static orientation scenario, where a person is matching a scene to a map to establish directional correspondence. The relative roles of salient landmarks and scene content and geometry, including space syntax isovist measures, are explored both in terms of general effects, individual differences between participant strategies, and the apparent cognitive processes involved. In general people tend to be distracted by salient 3D landmarks even when they know these will not be detectable on the map, but benefit from a salient 2D landmark whose geometry is present in both images. However, cluster analysis demonstrated clear variations in strategy and in the relative roles of the geometry and content of the scene. Results are discussed in the context of improving future geographic information content.