Why would a seventy year old retired Parsi judge of repute living in Bombay choose to spend a holiday in a war torn Mesopotamia in 1916? When Cursetjee Manockjee Cursetjee travelled from Bombay to Basra and back between 1916 and 1918, Basra was the base of British operations against the Ottoman Empire and the war in Mesopotamia had not yet turned conclusively in favour of the British. Yet, Cursetjee wrote confidently about the “capture and possession by our arms of practically all Mesopotamia”, emphasizing both British and Indian participation in the Mesopotamian arena of the First World War. Cursetjee’s travelogue is not simply a description of the ports and customs of the Persian Gulf, but a vivid characterization of “the Arab nature” as he sees it, leading up to a justification for why the next rulers of the Shat el Arab, recently liberated from the yoke of “Turkish misrule”, should be the British. I study Cursetjee’s travelogue, The Land of the Date: A recent Voyage from Bombay to Basra and back, fully descriptive of the ports and peoples of the Persian Gulf and the Shat’- el- Arab, their conditions, history and customs, as a text that encapsulates emergent twentieth century ideas about self determination and older nineteenth century ideas about empire as an ideal form of organizing trade and sovereignty in an awkward combination. As a language of interests begins to be employed as a precondition for effective governance, the best interests of the Arab population of the former Ottoman lands co mingles with British as well as Indian interests in Cursetjee’s evaluation. Importantly, Cursetjee’s representation of Indian claims to Mesopotamian lands is not imagined, and is echoed by the British Foreign Ministry as well, which attempts to strategically divert Indian attention away from Mesopotamia. This paper is an analysis of the political networks that shape routes of travel, the political purposes that a simple “holiday” of an imperial subject can be harnessed for, and the expansionary claims of Indians who earnestly entered the fray as the borders of the Ottoman empire came under question and the political geography of a region was sought to be altered.