Improvements in wireless infrastructures and personal mobile devices now make it possible for visitor sites to offer locative media experiences as an option for outdoor visitor experiences. However, while developing a design for such experiences is relatively easy, understanding how that design will play out in the real world is not. This chapter presents findings from three research engagements in which partners from the cultural heritage sector used a web-based tool to design and deploy locative media experiences. From thematic analysis of the findings, we show how our partners appropriated visualisations of digital footprints – geolocation data reported by visitors' mobile devices – to understand visitor behaviour and the interaction between the experience designs, wireless infrastructures and physical environment. We demonstrate how data interrogation "at the desk" and observation "in the field" can be combined in an effective cycle of iterative refinement, in an approach to location-based experience design that fitted around our partners' day-to-day work to manage outdoor visitor attractions.