This paper views the Internet as a platform that may be used in co-creating art experiences and to support player collaboration. Our research presents an ethnographic study of preschoolers testing an Augmented Reality mobile application that includes connected artworks as part of a Geocaching letterbox. Driven by belief in the power of play to support exploring, learning and development, and the conviction that competencies with digital technologies will be necessary to ensure future literacy skills, play with technologies has become an integral part of educational provision for young children in developed nations. New cultural services, such as location-based, urban experiences should convince players’, educators’, parents’ and the city’s policymakers of their value for playful engagement. Therefore, this paper aims to present a suggestion for how connectedness and collaboration can be supported through the Internet of Art in the context of playing on an augmented geocaching trail enhanced with artworks.