Based on ethnography of touristic encounters in Cuba, the article reflects on competing approaches to difference, inequality, and intimacy in tourism and in anthropology. Comparing the understandings of tourists and Cubans involved in these informal engagements, of the Cuban authorities, and of scholars and commentators, three idealized scenarios and modes of interpretation are teased out. Rather than assessing their degree of accuracy or suggesting the primacy of one over the other, the article reflects on their co-presence and competing rationales, focusing on the conditions of their emergence and assessing their epistemological, moral, and political implications. In so doing, it foregrounds how the expectations, desires, and moral underpinnings that inform our findings and interpretative horizons resonate with those of the people we study, opening up different possibilities for estrangement and familiarization, and highlighting what is at stake in these processes both for anthropology and for those with whom we work.