Literature by women of the third world is capable of expressing emergent feelings attached to objects and everyday activities, which reveal underlying economic processes. One such activity that inspires diverging feelings, the Caribbean vacation, reveals a continued exploitative colonial economy. Jamaica Kincaid’s essays in A Small Place dramatize the competing narratives of vacation as happiness object and misery-causing activities within the framework of the structure of terror. Many critics read differences of race and class developed through figures of the tourist and the native in the early essays as necessarily divisive post-colonial critique, but they read Kincaid’s final essay as an attempt to transcend such divisions. Many have lauded Kincaid’s call to throw off old categories and focus on shared (biological) humanity, yet this very category of “human” has been constructed through (social) discourses of race, gender, and class. Instead, I argue that Kincaid continues insisting on multiple subject positions, subverting the argument she seems to make on the surface and critiquing colonial epistemologies—in discourse and visual regimes—through application of Sylvia Wynter’s interrogation of dominant worldviews of both humanism and an approach to environments.