When conveying information about spatial situations and goals, speakers adapt flexibly to their addressee in order to reach the communicative goal efficiently and effortlessly. Our aim is to equip a dialogue system with the abilities required for such a natural, adaptive dialogue. In this paper we investigate the strategies people use to convey route information in relation to a map by presenting two parallel studies involving human–human and human–computer interaction. We compare the instructions given to a human interaction partner with those given to a dialogue system which reacts by basic verbal responses and dynamic visualization of the route in the map. The language produced by human route givers is analyzed with respect to a range of communicative as well as cognitively crucial features, particularly perspective choice and references to locations across levels of granularity. Results reveal that speakers produce systematically different instructions with respect to these features, depending on the nature of the interaction partner, human or dialogue system. Our further analysis of clarification and reference resolution strategies produced by human route followers provides insights into dialogue strategies that future systems should be equipped with.