This contribution will present pedagogical methodologies and strategies used to introduce Caribbean texts to undergraduate students from the Université de La Réunion in the Indian ocean. My primary aim in the selection of texts provided to the students was to foster transoceanic dialogues between Caribbean and Indian ocean (literary) histories and invite students to engage with forms of transcolonial interconnectedness. Caribbean authors were selected as part of a module on postcolonial literature ("Littérature des Pays Anglophones") and put in a dialogue with other language and content-based modules, respectively translation (thème & version) and British literature. Charlotte Brontë's Jane Eyre was introduced to the students as part of the British literature module, in an attempt to (re)connect Western classics with some of their postcolonial reworkings, such as Jean Rhys’s Wide Sargasso Sea. However, the aim was not so much to establish vertical connections between centre and periphery as to invite students to think latitudinally about Caribbean and Indian ocean literatures. To do so, the themes of madness, slavery and indentured labour, as well as orality and creole languages, particularly through the genres of poetry and dub-poetry, were explored in twentieth-century writing to establish connections between Caribbean and Indian ocean (post)colonial experiences. Translation classes further served to question and debate possible strategies of transposing Caribbean/Indian ocean specificities for Western and non-Western audiences. These language classes also invited students to further explore the situatedness of creole/non-creole languages whilst initiating them to a trans-archipelagic assessment of so-called “postcolonial” studies.