This essay explores how authors, texts, and forms moved throughout the Caribbean in the period, transgressing boundaries of language and geography. Regional responses to the Haitian Revolution and other Caribbean antislavery and anticolonial movements reveal the clear trans-Caribbean focus of many nineteenth-century Caribbean writers. Additionally, the growing sphere of newspapers provided a concrete means through which ideas circulated throughout the region. This chapter looks primarily to Haiti and Trinidad as early examples through which to consider literary anglophone–francophone connections and the formations of Caribbean identity that heavily influenced later Caribbean writers. I argue that the circulation of ideas and authors in the period ultimately generated complex negotiation of contested spaces, shifting boundaries, and complex identities that gave rise to conceptions of creoleness and exile that are foundational to Caribbean literature.