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This research uses participant observation and other qualitative methods to evaluate whether faculty-led short-term study abroad programs can successfully carry out responsible ‘fair trade’, and thereby substantially benefit not only students but also the host communities. The research draws insights by comparing two experiential learning courses taught in South Africa and Dominica. Results suggest that students benefit in various transformative ways in both courses, by applying sustainability and development studies concepts to real-life service and hands-on learning in cross-cultural situations. The Dominica course yields more host community benefits, however, because of the instructors’ long-term commitments to reciprocal partnerships and equitable engagement. The paper concludes with recommendations for enhancing the impacts of short-term study abroad on students and, especially, on their host communities.