This article reflects upon Richard Price’s newest work, Travels with Tooy. In it, the author argues that the book – on the surface, a text about the transmission of esoteric knowledge passed down from “First Time” to the present among Saramaka Maroons – is actually an investigation of the role of anthropological knowledge within Caribbean Studies. As such, Travels opens a window on the anthropological contribution to more general debates about nation-building throughout the circum-Caribbean. The author tracks anthropology’s disciplinary history vis-à-vis the Caribbean in order to explore some of the roads not traveled within Travels. This is done to highlight the ways issues emerge and change across generational cohorts of researchers. The author concludes by arguing that anthropology’s continued relevance to Caribbean Studies depends on rethinking some of our main areas of focus and methods of engagement.