This chapter investigates how the transnational crossings Elizabeth Bishop launched from the peninsular Florida and its Key into Haiti, Mexico, Aruba, and most famously, Brazil, across North & South, Questions of Travel and Geography III correspond to an analogous geographical arc on the part of Audre Lorde, in which the Southeastern United States, Oaxaca, Mexico, and the Virgin Islands inform an equally fluid and indeed oceanic space from her work of the 1980s onward, when Lorde began spending significant time in the Virgin Islands. As Bishop sought to ‘do more’ with Key West and its environs in than modernist predecessors like Wallace Stevens and Hart Crane by employing this island to make investments in gender, race, nation, and class, Audre Lorde brought racial and sexual difference to the fore of this liminal crossing across national borders and boundaries, hybridizing her own better documented investments in Yoruba myth with a trans-American consciousness lodged squarely in not only the Caribbean and the Southeast, but in Oaxaca, Mexico and the Southwest. Such a remapping reveals two outsider poets who stand at the center of a literary formation where twentieth century American and African-American poetics converge and clash.