The Caribbean has long afforded U.S. and Canadian geographers with a rich venue of study-abroad opportunities. Physical and human geography classes are particularly well-suited to the myriad political, social, and environmental landscapes of the region. This article summarizes a few key experiences that have emerged in forging study-abroad venues in the Dominican Republic and Cuba. In the latter, the norms of operation have always been nebulous. Avoiding criticisms of the Castro government is paramount, accommodating tour-guide spies is often necessary, and getting away from the top-down party line is essential. In the former, we describe a study-abroad site that is, culturally at least, so similar to eastern Cuba that it is uncanny. However, the low presence of public institutions and the prevalence of strong corporate agents impose another set of obstacles that must be carefully traversed. The case studies illustrate how geographic field research cannot be divorced from broader political, economic, and corporate interests and that how geographers grapple with these matters should not be done out of the students' view. Rather, with the use of discretion, these obstacles can provide valuable "teaching moments" that are the backbone of international education. (Contains 1 table, 1 figure and 2 notes.)