This essay brings into dialogue discrete conversations in Caribbean studies, international political economy (IPE), and hemispheric American studies. Contextualizing these fields through the trope of hospitality, a figure of particular significance in Caribbean-U.S. relations, the author charts a field of writing he terms Caribbean American Regionalism, which is not bound necessarily to the geographic or ideological commitments of U.S. regionalist traditions even as it acknowledges and extends from innovative scholarship about them. The essay focuses on the role of women's voices in such a regionalist, Caribbean American imaginary, specifically Jamaican Creole healer and boarding-house operator Mary Seacole and the Eurasian writer Sui Sin Far. Although from distinct epochs and locations, Seacole and Sui Sin Far—as migrant laboring women of color in the Caribbean American region—are affected by, and their texts keenly respond to, developments in Caribbean-U.S. relations during the last half of the nineteenth century. This is particularly so in light of the dependence of corporations like the Panama Railroad Company and United Fruit Company on commodities produced by, and on the commodifying the bodies of, laboring West Indian women in hospitality industries. Seacole and Sui Sin Far, by marking (in)hospitable relations in the Caribbean American region in sites of hospitality where they reside and work—the Jamaican creole boarding-house and tourist hotel, respectively—expose the (in)hospitality of industry and the industry of (in)hospitality sponsoring nineteenth-century U. S. expansionism.