Maps are an important component within many of the playful and gameful experiences designed to turn cities into a playable infrastructures. They take advantage of the fact that the technology used for obtaining accurate spatial information, such as GPS receivers and magnetometers (digital compasses), are now so wide-spread that they are considered as ‘standard’ sensors on mobile phones, which are themselves ubiquitous. Interactive digital maps, therefore, are are widely used by the general public for a variety of purposes. However, despite the rich design history of cartography digital maps typically exhibit a dominant aesthetic that has been de-signed to serve the usability and utility requirements of turn-by-turn urban navigation, which is itself driven by the proliferation of in-car and personal navigation services. The navigation aesthetic is now widespread across almost all spatial applications, even where a be-spoke cartographic product would be better suited. In this chapter we seek to challenge this by exploring novel neo-cartographic ap-proaches to making maps for use within playful and gameful experi-ences designed for the cities. We will examine the potential of de-sign approaches that can producte not only more aesthetically pleasing maps, but also offer the potential for influencing user be-haviour, which can be used to promote emotional engagement and exploration in playable city experiences.