The nineteenth century saw not only a precipitous rise in travel, but also in writings about travel. This was especially true for Cuba, a popular destination for Americans seeking health and pleasure. Writings on Cuba typically took the form of guidebooks, travelogues, and diaries. While these writings sought principally to inform readers about the sights and sceneries of the island, they were also, in the words of Louis A. Pérez, “rich with implication” in that they expressed the writers’ subjective impressions of the locales they visited as well as ruminations on the social institutions and cultural practices of the day—Cuban as well as American. This body of literature heralded an emerging public awareness of globally scaled social issues as well as speculation about optimal outcomes for Cuba, the United States, and the world. This chapter explores cultural motifs to which travel writers often referred—specifically bullfights, cockfights, Sabbath laxity, and barred windows as emblems of a degenerate Spanish “otherness”—and proposes that through repetition and insinuation, these motifs contributed to the construction of U.S.-Cuba conflict, particularly with regards to colonialism and questions of moral superiority.