Though critiques of conventional study abroad are not new, the growing emphasis on learning outcomes draw attention to what – and how – students learn from their international experiences. Assumed benefits are being confronted, and some are asking whether the investments are worth it. This places attention on how schools justify, organize, implement and assess study abroad programs. This paper examines the experiences of an unconventional, short-term learning abroad program to Istanbul/Turkey– characterized as a faculty-led, immersion program – in the summers of 2011, 2012 and the winter of 2013. Each trip requires a semester of preparation. The emphasis of the program is on experiencing and learning about daily life in Turkey, valuing non-U.S/non-European ways of doing things, on understanding and building relationships with place, and confronting such problematic things as stereotype, privilege, exceptionalism, and the consumption of culture. Applying the critical literature to the author’s observations leading the evolving program, the paper investigates the implications of “faculty-led” and “immersion,” highlights opportunities and potential benefits, and presents the difficulties and tensions of learning