One of the major questions that Black diaspora studies addresses is what it means to foreground the oceanic space of the Atlantic as a historical site of violence in our understanding of Western modernity. Centering on the historical rupture of slavery and the Middle Passage, the Black Atlantic paradigm precipitates a transnational approach to the study of the cultural, political, and intellectual itineraries across the Atlantic and the Americas. An archipelago embroiled in a long history of colonialism, slavery, and creolization, the Caribbean has emerged as a crucial nexus in the transatlantic network with a robust intellectual tradition. However, while much scholarship has followed the transcultural framework of the Black Atlantic and understood the region as a formative crucible characterized by fluidity, mobility, and creolized identities, diasporic criticism tends to reduce the ocean to a static backdrop in its privileging of large landmasses over small isles and has yet to recognize how the Caribbean intellectual tradition is rooted in an oceanic logic of archipelagic thinking. Reclaiming the open insularity of the Caribbean to complicate the boundedness of island space, my dissertation takes the form of the archipelago as a heuristic device to remap the terraqueous geographies of the Black diaspora in its entanglements between sea and land, roots and routes, islands and continents. Curating a constellation of Caribbean island writings that foregrounds the relationality of islands, oceans, and continents, Caribbean Archipelagraphy engages with the archipelagic thinking to decenter the paradigm of the Black Atlantic and interrogates the colonial discourses of island isolation and continental exceptionalism that render the entire region remote and peripheral to modernity. Offering new theorizations of the Black diaspora through the concept of the archipelago, my dissertation further formulates the concept of “imperial intimacies” to emphasize the durabilities of imperial relations not only in the geopolitical realities but also in the most private sphere of intimacy. Throughout the dissertation, the concept of imperial intimacies serves to illuminate the inter-imperial rivalries and collaborations between European and U.S. empires, the normative scripts of desire in the post/colonial Caribbean, and the cross-racial mutuality or other forms of intimacies that emerge from forced and voluntary transoceanic migrations. Navigating the differential scales of islands, oceans, and continents, Caribbean Archipelagraphy traces a palimpsest of imperial intimacies to disrupt the epistemological limits of colonial archives. It argues that Caribbean archipelagic writings by Eric Walrond, Claude McKay, Zora Neale Hurston, and Paule Marshall engage in alternative cartographical practice to recenter island geography and its intimate landscapes as crucial to our understanding of modernity in the imperial longue durée. Interrogating the historical amnesia of imperial modernity, my dissertation complicates the teleological trajectory of postcolonial sovereignty and engages with unacknowledged repositories of historical memory to rethink the discourses of modernity and liberal humanism as inextricable from the legacies of colonialism, slavery, plantation economy, and neo/colonial governance across the twentieth century.