As international educators, the overwhelmingly urban context of study abroad requires not only a more intense querying of "the city" as a concept, but also more attention to how students could engage with and learn from the urban landscape. In this article, the authors begin with a theoretical flanerie through a range of ideas related to the city in order to frame programmatic strategies for promoting a more critical student engagement with urban spaces and places. They pay particular attention to the fact that students now come into study abroad cities armed with a battery of technological tools, unlike their 19th century counterpart. They question whether students are employing these tools to engage with the spaces and places of locality or simply creating endless images and representations about these abroad cities without any real thought or connection. They aim to provoke thought about how they might profitably harness the possibilities of students' new media use toward their pedagogical ends. They therefore cover both theoretical and practical matters to encourage practitioners to infuse programming with increased local specificity as they welcome the current generation of study abroad participants into what is still a plethora of urban difference.