Understanding better the effects of the use of mobile apps to the use and appreciation of urban environments has been gaining more prominence as a research topic recently due to the increasing everyday use of these apps. Whether this type of digital mediation changes the lived experience is of interest in this article. The intention is to show that besides changing the prevailing practices and behaviour, new technologies also enhance and add positive value to the everyday urban experience. This positive experiential value is approached with the framework consisting of recent advances in philosophical urban and everyday aesthetics, which put emphasis on both familiarity and fun as important qualities that describe the everyday experience in urban environments. We claim that new digital tools increase the quality of fun when moving in familiar surroundings. Fun, understood through the lens of the aesthetic, precedes the experienced quality of playfulness. It alters the existing affordances of the urban environment in a way that make more complex aesthetic qualities emerge. The case examples are GPS-based wayfinding applications such as route planners and navigation tools for pedestrian use and related AR applications such as the popular game app Pok?mon GO.
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