  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.
