Against a background discussion on mainstream poetry, this study offers insights on the venture of the Palestinian poet Mahmud Darwish (1941–2008) into the realm of Middle Eastern mysticism, handed down to us as “Sufism.” Darwish sets aside discourse concerning religion, although he leans on the scripture of more than one system of belief. In his poem Abī (My Father), the poet tells us of Shi‘a observance as he experienced it; and, in his poem Abad al-Ṣabbār (The Eternity of Cactus), the poet compares the Palestinian 1948 Nakba (Tragedy) to the massacre at Karbala in early Islamic times. Poems such as al-Hudhud (The Hoopoe) and the collection Ward Aqall (Fewer Roses) fall into place. These poems, which mark the onset of Darwish’s mature period, are not understood as well as his earlier output. In some measure, this could be because translators to English have ignored the poet’s clearly stated requirements for translating his poems.