Digital storytelling has been extensively used in cultural heritage sites with the aim to construct knowledge about the past and promote its significance to the present. From the body of research and practical implementations that are concerned with hybrid forms of storytelling in cultural heritage sites, only a few systematically explore the interplay between narrative form and space. Focusing on the interactive paradox as it manifests in the connection between the narrative structure and the physical space of heritage sites, this paper explores the theory and practice of place-based storytelling and provides an analytic and comparative discussion based on best practice examples in an attempt to identify current challenges and lessons learnt.