The major purpose of this study was to investigate the challenges posed by cultural expressions in translating the play Nitaolewa Nikipenda from English into Kiswahili. The study employed the Cultural theory of translation (CTT) which asserts that translation of literary text became a transaction not only between two linguistic substitutions but also a negotiation between two cultures. The findings indicate that, social habits and practices like dances and ceremonies, greetings, feeding habits, shelter, technology, ornaments and decoration, religious and legal aspects are culturally induced and therefore, the language used to express them always reflect the cultural values of a particular social community. In this case, the transfer of these cultural expressions was a challenge to a translator of the selected play. However, through this study it has been proposed that translators can adopt various strategies such as the use of cultural transfer, borrowing and footnote so that they can at least minimize the problem. The study through the play Nitaolewa Nikipenda concludes that, cultural expressions pose an acute barrier to proper translation.