Vacationing is the event where most photographs are taken (Baerenholt et al. 2004) as taking pictures is an important way in which the tourist gaze is enacted. According to Urry (2002), the tourist gaze, or the ways of seeing, identifies what is the “extraordinary” and the “other” in the tourist experience. Therefore, residents and tourists may portray or perceive a tourism destination differently. Using social semiotics as a methodological framework, this paper analyzes the photographs posted by residents and tourists in the context of Old San Juan, an important historic destination in Puerto Rico, to identify commonalities and differences. A total of 1,064 photographs were analyzed for this study.