Maps are an important component within many of the playful and gameful experiences designed to turn cities into playable infrastructures. They take advantage of the fact that the technologies used for obtaining accurate spatial information, such as GPS receivers and magnetometers (digital compasses), are now so widespread that they are considered as ‘standard’ sensors on mobile phones, which are themselves ubiquitous. Interactive digital maps, therefore, 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 designed 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 bespoke cartographic product would be better suited. In this chapter we seek to challenge this by exploring novel neocartographic approaches to making maps for use within playful and gameful experiences designed for the cities. We will examine the potential of design approaches that can produce not only more aesthetically pleasing maps, but also offer the potential for influencing user behaviour, which can be used to promote emotional engagement and exploration in playable city experiences.