The Internet of Art as in public and connected art installations gives birth to interactivity and participation, which in turn, introduce new challenges, not only to the production of artworks, but also in how to involve the participants and how to evaluate the results of target experiences, such as social connectedness, context, playfulness, and gamification. This case study presents an example of interactive and participatory forms of the Internet of Art. We have used a multimethod approach including qualitative research methods to understand preschool-aged children’s experiences who used the Sigrid-Secrets Augmented Reality application in playing the game of geocaching and finding physical artworks prior to the geocache. We have observed two groups of preschoolers play-testing, analysed the videotaped documentation of the testing, and followed the children drawing their memorable experiences of the geocaching trail. By using the Playful Experiences (PLEX) framework, we have evaluated the preschoolers’ memorable experiences of playing. Our findings demonstrate how augmented techniques can be used to transform the physical surroundings in order to create a hybrid game-world suited for learning and fun. In this game-world the player can become immersed in the flow of playful experiences, and engage with edutaining exercises while being simultaneously connected to both to the Internet of Art and to the physical dimensions of the real world environment.