Utilizing Romanticist, postcolonial, and feminist literary criticism, this project posits the interconnectedness of ideologies of family, inheritance, domesticity, gender, sexuality, and race as central to the construction of notions of nation and family in both Romantic-era literature and contemporary Caribbean writing. I use novels by twentieth-century Caribbean women writers Jean Rhys, Michelle Cliff, and Jamaica Kincaid as sites of entry into some of the most hotly contested issues in transatlantic studies. The twentieth-century novels I examine provide insight into the policing of boundaries of gender, sexuality, and race as the English and the Afro-Caribbean family and cultures became intertwined through slavery and colonization. Chapter One argues that Jean Rhys' novel, Wide Sargasso Sea , intervenes in a long line of Romantic-era novels such as Maria Edgeworth's Belinda , Mary Hays' Emma Courtney and Jane Austen's Mansfield Park , that express English women's fear of the contamination of colonialism and slavery in the domestic sphere. In tracing this historical legacy, I provide a new reading of Charlotte Brontë's Jane Eyre that shows it to be the inheritor of Romantic-era discourses of domesticity and slavery, rather than the initiator of these themes in British women's writing. In Chapter Two I explore Michelle Cliff's use of intertextual references to Walter Scott's Ivanhoe in her novel Abeng in order to critique gendered meanings of Romantic nationalism, revolution, and race within the West Indian family. Cliff's Jamaican characters' attempts to invoke a Romantic nationalism based on connection to place, family, and the folk cannot have the same meaning in Jamaica, her second novel No Telephone to Heaven suggests, as in Romantic ideology. Chapter Three explores the teaching of William Wordsworth's poetry in colonial classrooms as constituting a pedagogy of Englishness divisive to a Caribbean sense of family and place, as Jamaica Kincaid's works Lucy and A Small Place demonstrate. By arguing that the Romantic period constitutes a crucial but overlooked historical touchstone in the context of the Anglophone Caribbean, my project connects discourses, genres and modes of thought usually theorized as separate academic specialties.