“Midsummer XXVII” explores the effects of colonization on the Caribbean Islands’ culture and on the speaker personally. Presumably, the speaker is an avatar for Derek Walcott himself, who found himself between worlds and cultures. Walcott had grandparents of both European and African descent. He was raised on St. Lucia but went to school in English-speaking institutions where he studied Shakespeare and British literature. He taught in Boston and made his career and home in the Northern Hemisphere half of the time but returned to Trinidad and the islands in the summers. As in many of Walcott’s poems, the speaker of “Midsummer XXVII” feels ill-at-ease among these shifting cultural identities.

The poem is set on St. Thomas, an island that has a long history of colonization. Originally inhabited by the Ciboney, and then by the Carib and Arawak, all Indigenous peoples, the island was colonized by Europeans in the 1500s. British, French, and Dutch interests took control of all of the islands in the region. On St. Lucia, where Walcott was born and raised, the French and British continued to fight for control. On St. Thomas, the Dutch and British had competing influences. European powers used their strongholds in the islands to build sugar plantations and import enslaved people from Africa.