Caribbean literature relies on the reader's capacity to identify elements of the textual landscape and interpret them within appropriate environmental, cultural and historical contexts. The pedagogical approaches discussed in this paper are taken from The Island School's [Bahamas] Literature of the Sea course which features an intensive study of St Lucian poet Derek Walcott's epic Omeros. Curriculum is designed to help students access these elements of the text through observation and direct interaction. The methodologies set forth in this paper are the result of experiences in a unique educational context but are widely applicable. Results demonstrate that student outcomes improve with the opportunity to interpret Caribbean literature through immersion experiences in the natural and cultural environments of the texts.