Wayfinding, or the ability to plan and navigate a course over the landscape, is a subject of investigation in geography, neurophysiology, psychology, urban planning, and landscape design. With the prevalence of GPS‐assisted navigation systems, or “wayfinders,” computer scientists are also increasingly interested in understanding how people plan their movements and guide others. However, the importance of wayfinding as a process that regulates human mobility has only recently been incorporated into archeological research design. Hominin groups were able to disperse widely during the course of prehistory. The scope of these dispersals speaks to the innate navigation abilities of hominins. Their long‐term success must have depended on an ability to communicate spatial information effectively. Here, we consider the extent to which some landscapes may have been more conducive to wayfinding than others. We also describe a tool we have created for quantifying landscape legibility (sensu Gollege), a complex and under‐explored concept in archeology, with a view to investigating the impact of landscape structure on human wayfinding and thus, patterns of dispersal during prehistory. To this end, we have developed a method for quantifying legibility using a Geographic Information System (GIS) and apply it to a test case in prehistoric Iberia.