Retail is one of the defining elements of urban spaces. The study of commerce is largely based on its evolution and how it relates with urban environments. Currently, with the advent of mass tourism, there has been an adjustment in the commercial fabric of the area’s most sought after by tourists. Among these latter areas, the historical centers of commerce stand out. The first objective of this research is to analyze the modern evolution of the commercial fabric of Lisbon by comparing the city center with the rest of the city. For this goal, I use a quantitative approach through the quotient location for specific retail typologies. The results show dissimilarities that are associated with the geographical location of retail, which vary according to the different retail typologies being analyzed. The second goal is based on the assumption that the mere analysis of the evolution of the retail typologies is limited in the context of tourist cities. Considering this matter, a qualitative method (photo analysis, conceptually supported by the concept of authenticity) is used. The results show the usefulness of the concept of authenticity to apprehend and discuss how retail is reacting to the tourism industry, thereby contributing to the transformation of the city center into a leisure and entertainment destination.