Histories of West Indian writing have traditionally put particular focus on the migration of a group of writers often labelled in shorthand as the Windrush generation, after the 1948 arrival of the Empire Windrush that began the post-World War II arrival of large amounts of Caribbean people in Britain. Finding opportunities in the British literary scene – most notably, with the BBC’s Caribbean Voices programme – these migrant writers were able to establish themselves, promote each other, and reach a wide audience, even as their encounter with British racism intensified their anticolonial vision. These writers’ experience was frequently refracted through the idea of exile, which in the Caribbean critical imaginary came to define the writers of the period. This chapter takes up an examination of this remarkably prolific and influential generation of anglophone Caribbean writers, with particular focus on the extent to which exile is an adequate concept for thinking about their writing. It discusses the different levels of geographical and cultural identification with which these writers grappled, remarking the process by which interacting with Caribbean people from throughout the region in Britain helped foster a West Indian cultural identity beyond any single island, as well as the tension between regionalism and localized nationalism that resulted. Going further, it will also illustrate the sense of an emergent ‘rooting’ of the Caribbean in Britain, a process that was self-consciously addressed in the writing of many of these authors and subsequently formalized in the formation of alternative publishing and cultural institutions in Britain in the 1960s and 1970s. The chapter provides readings of works by Kamau Brathwaite, George Lamming, V. S. Naipaul, Andrew Salkey, and Samuel Selvon, and puts them into context with the much larger population of less celebrated writers, as well as Caribbean literary figures who came to England before the post-World War II period of mass migration. In illustrating the complexity of the Windrush writers’ engagements with notions of home, citizenship, belonging, and cultural ownership, the essay argues that a more fluid, multi-directional understanding of the concept of exile is necessary in order for the era’s important contributions, not just to the project of anticolonial nationalism, but also to the nascent discourses of diaspora and black Britishness, to be properly understood.