Creating first hand experiences of urban cultures that focus on reflection and leave profound impressions on students while providing the framing for future cycles of experiential learning is a complex and difficult dynamic to navigate. The way urban manifestations of a different culture are directly experienced varies depending on the circumstances of a concrete cross-cultural encounter and the student's subjective interpretation of it. To suggest a tentative framework within which the elusive nature of interpreting an urban culture can be channeled, facilitated, and made fertile for effective teaching, in this article the author turns to his on-going study conducted in Berlin, Germany. The specific study abroad program under investigation is designed around the study of the European metropolis. The author focuses on the role and considerations of teachers who approach urban cultures by creating episodes of experiential learning. First, he elaborates on experiential learning theory and the philosophy of experiential education as two concepts that highlight complex teacher-student-environment reciprocities. Second, the discussion of an interview, read against other interviews and the theory of experiential learning, demonstrates the challenges of designing and conducting experiential learning situations. The ensuing discussion of best practices in mediating urban cultures will validate the city's capacity for experiential learning and reveal solutions for the intercultural hurdles involved in teaching "experientially." Ultimately, the author argues that more effort is required to close the gap between the theoretical and practical considerations of the experiential teaching of urban cultures in order to safeguard positive learning outcomes and increase the efficiency of teaching and learning in study abroad courses.