Although spatial reasoning is developed through interaction with the real world, many studies focus on abstract spatial skills which exhibit a moderate relationship with real-world skills. In the present study, we explore links between middle-school student performance on abstract and authentic spatial tasks. Thirty students from three geographically diverse settings demonstrated their perspective-taking skills with local landmarks and how these relate to an abstract perspective-taking task. Rural and regional students demonstrated accurate estimations for landmark locations relative to urban students. The use of spatial tools such as gesture, language, and spatial relations were analyzed to explore student processing during the task. Our findings suggest that the connection between abstract and authentic tasks is not always straight-forward. Students from rural and regional areas demonstrated robust knowledge of their local environment with evidence for meaningful connections embedded in sociocultural and geographic experiences. By contrast, more urban students were able to apply sound spatial strategies when completing the abstract task but struggled to apply these strategies without the local knowledge or awareness of their position in space. We propose that often-neglected authentic spatial tasks assess a different, but critical element of spatial skills needed for navigating the world around us.