This article analyzes the impact of experiential and inquiry-based learning exercises in a 2019 Toronto study abroad course on smart cities for first-year students. The course treated the city as a text to be read, analyzed, and unpacked. Students engaged with the disciplines of urban studies, critical race and ethnic studies, and surveillance studies in order to assess Toronto's smart city initiative while exploring firsthand how technology and urban planning currently structure the lived experiences of Toronto's inhabitants. Ultimately, students came to understand how data analytics order, pattern, and structure the complexity of urban life in ways that can be inclusionary and exclusionary, democratic and autocratic. They gained an appreciation for why a range of stakeholders with disparate social and economic power perceive smart city initiatives differently, and they theorized what it might mean to live in a wise city that accounts for history, ethics, and power.