Undergraduate geography courses provide a significant entry way into representing and challenging dominant images of places and identities. Teaching geography in the Caribbean raises significant issues in terms of providing materials that explore representations of places and topics that are grounded in the region, while also moving beyond representations of islands as simply 'Third World', separate and distant. The author draws on the case study of teaching human geography courses at the University of the West Indies-Mona, to explore the usefulness of transnationalism as a pedagogical framework--in conjunction with the use of films and fieldtrips--while examining processes of representation and neo-colonialism.