Drawing on an extended road trip from England to India undertaken by two Indian travellers in the 1950s, this paper challenges the dominant travel stories and Eurocentric academic accounts that persistently privilege western tourists. Focusing upon the literary desires that shaped their British itinerary and a dramatic encounter in Egypt, we highlight two distinctly different experiences that emerged during their journey. We demonstrate how a swirl of larger historical events and processes marked the time in which they travelled, with the encounters, places and incidents they experienced informed by the dissipation of colonial alliances and the emergence of postcolonial connections.