Navigation is essential to life, and it is cognitively complex, drawing on abilities such as prospective and situated planning, spatial memory, location recognition, and real-time decision-making. In many cases, day-to-day navigation is embedded in a social context where cognition and behavior are shaped by others, but the great majority of existing research in spatial cognition has focused on individuals. The two studies we report here contribute to our understanding of social wayfinding, assessing the performance of paired and individual navigators on a real-world wayfinding task in which they were instructed to minimize time and distance traveled. In the first study, we recruited 30 pairs of friends (familiar dyads); in the second, we recruited 30 solo participants (individuals). We compare the two studies to the results of an earlier study of 30 pairs of strangers (unfamiliar dyads). We draw out differences in performance with respect to spatial, social, and cognitive considerations. Of the three conditions, solo participants were least successful in reaching the destination accurately on their initial attempt. Friends traveled more efficiently than either strangers or individuals. Working with a partner also appeared to lend confidence to wayfinders: dyads of either familiarity type were more persistent than individuals in the navigation task, even after encountering challenges or making incorrect attempts. Route selection was additionally impacted by route complexity and unfamiliarity with the study area. Navigators explicitly used ease of remembering as a planning criterion, and the resulting differences in route complexity likely influenced success during enacted navigation.