Travel writing is very much a thriving genre of literature in our times, and the issues brought about by a large-scale global movement of peoples and the existence of expatriate communities are already found in the travelogues that some of us are working on. Travel writers were often multicultural individuals who attempted to negotiate the differences and distances between cultures, but also between expatriate communities and the homeland. I propose to examine a travelogue by a Greek subject of the Ottoman Sultan, Demetra Vaka Brown. Her travelogue Haremlik published in 1909 chronicles her first trip back to Constantinople after a six year absence. In trying to explain her native city to her American audience Vaka Brown attempts to negotiate the differences and distances between Turk and Greek to create affinities between Greek and American. She walks a fine line where she claims authority and access to authentic information because she is from there and yet she emphasizes that she is not one of them. Her being an outsider at home helps to make her an insider abroad, which then becomes her new home. Demetra Vaka Brown’s work allows us a more nuanced view of relations between the Greek and Muslim women’s interactions as well as a more complex view of the encounter between the East and modernity within Ottoman households.