The need for and challenges of teaching artificial intelligence (AI) at primary, secondary, and upper-secondary levels have been a major focus of recent academic discussions [1],[2],[3]. Often referred to as AI4K12 [4], this area explores global initiatives that introduce AI to students from kindergarten through high school. The rapid advancements in deep learning and generative AI technologies suggest AI will become a transformative force. This realisation has prompted governments and policymakers to recognise the need to prepare future citizens for a world heavily influenced by AI. As AI becomes increasingly integrated into information systems, concerns are mounting about citizens' ability to use these systems responsibly and understand the consequences of not doing so [5]. Furthermore, anxieties regarding AI's potential impact on societal sustainability highlight the need to equip future workforces with the skills to combine human creativity with AI's potential to create sustainable systems.

The HCI field has demonstrated a growing interest in leveraging emerging technologies to enrich urban experiences. However, insufficient studies investigate the experience and design space of AI image technology (AIGT) applications for playful urban interaction, despite its widespread adoption. To explore this gap, we conducted an exploratory study involving four participants who wandered and photographed within Eindhoven Centre and interacted with an image-to-image AI. Preliminary findings present their observations, the effect of their familiarity with places, and how AIGT becomes an explorer's tool or co-speculator. We then highlight AIGT's capability of supporting playfulness, reimaginations, and rediscoveries of places through defamiliarizing and familiarizing cityscapes. Additionally, we propose the metaphor AIGT as a 'tourist' to discuss its opportunities for engaging explorations and risks of stereotyping places. Collectively, our research provides initial empirical insights and design considerations, inspiring future HCI endeavors for creating urban play with generative AI.