The present study investigates the semantic, syntactic and figurative challenges that pose difficulty to the two translators of Midaq Alley into English, particularly in the extracts that describe the setting of the novel. The two translations examined are Trevor Le Gassick’s (a revised edition published in 1992) and Humphrey Davies’ (2011). Several problematic extracts are selected to discuss the difficulties involved. The difficulties are tackled on three levels: semantic, figurative and syntactical. The semantic level includes subtleties and shades of meaning among different lexical choices made by the two translators. This level also includes culture-specific items; religious and Qur’anic expressions; and juxtaposition of Classical Arabic and MSA or Cairene lexical items. The figurative level includes the tropes that the ST makes use of as an emblem of literary texts. This includes, but is not limited to, metaphors, hyperboles, etc. The syntactical level is concerned with the syntactic structures and the sentential shifts that occur due to the diversity of the translation strategies adopted at the sentential level. Strategies of translation adopted are also analyzed in tandem with all the above levels. The study concludes that Le Gassick has taken liberties with the ST, very often omitting, compressing and chunking, while Davies has stuck to the letter of the original, thus copying the ST structure as much as possible.