This paper focuses on Caribbean boat people, who are being victimized by state/society politics at home and abroad, and who seek a line of escape across treacherous ocean routes to the North or South. Migration literature explains these movements, in terms of forms of displacement deriving from the push and pull of development. Such a casting reflects the post-colonial (nation)-states’ pursuit of “freedom’s charms” in the alchemy of becoming “First World.” Yet another reading is possible and necessary. I suggest that these hope-filled mo(ve)ments, often risking tragic encounters with death, also require one to investigate the socio-cultural imaginaries entangled in these (dis) placements and movements. I see these socio-cultural imaginaries as ways of interpreting that reflect lived modes of writing and conducting existence, or one’s place in the world, rather than manifesting “explicit ideologies” (Salazar 8, Gaonkar). By way of rethinking the structuring of migrants’ movements through visual, poetic, and cultural religious practices I seek to explore these imaginaries as quests by Caribbean boat people for elusive dreams of freedom. I also offer to apprehend their movements through an optic of the will-to-place — a certain kind of political consciousness instrumentalized through cultural forms. This approach allows for an exploration of the challenges to the expression of this will in terms of struggles for “citizenness,” or a place in modern freedom, and against the disorders of contemporary neo-liberal governmentalities, marked by the marketization of social relations and the contractualization of citizenship.