Thom Andersen’s Los Angeles Plays Itself (2003), hailed as „a city symphony in reverse,” challenges whether the movies have ever really depicted Los Angeles. I attempt to address a similar question in my present work, which focuses on travel writing: do Petru Cormarnescu in America as Seen by a Young Man of Today (1934) and Stelian Tănase in his L.A. vs. N.Y. (1998) truly see the city of Los Angeles? Drawing on research in the field of travel writing studies, my study examines how the Romanian travelers’ cultural encounters triggered both processes of representation and misrepresentation and gave rise to varying cultural constructions of place. This is tied to the fact that making the new and unfamiliar meaningful presupposes a continuous process of ‘translation’ laden with approximations, misconceptions, distortions, half-truths, and varying authenticities. When the travelers sought to pin down otherness, it was the familiar that resurfaced, and the cultural heritage of the place left behind ‘taught’ the travelers what and how to see. In doing so, travel writings could best exemplify that cultural boundaries are fluid, permanently drawn, and redefined.