The Caribbean DiasporaDiasporaCaribbean, according to Stuart Hall, is a place of identity negotiation; these are enclaves of Caribbean immigrants in places like New York, Toronto and London, where the Caribbean reproduces itself through the identities that people bring and enact. Within the DiasporaDiaspora are individuals who each have their own diasporic journeys. In this chapter I describe my diasporic journey travelling with my internalized home while searching for an academic home. Through letters I speak to the different spaces that have shaped my identity and through narrative I tell of my experiences across these spaces and time. My journey is a continuation of the pathway my elders and ancestors forged and that has allowed me to learn more about my identity as a Caribbean, as a Black woman and as an academic.