Based on the premise that pictures are not only culturally but also economically meaningful in the context of tourism, this article proposes a rearrangement of MacCannell’s model “semiotics of attraction” to discuss current negotiations of meaning of sight/site marking with urban photography. In Detroit, the city’s negative image has changed from ill-reputed urban wasteland to picturesque ruinscape of “America’s Great Comeback City.” Turning the post-industrial shrinking city into a tourist attraction has not resolved socio-economic problems but instead commodified them. Carving out the underlying neoliberal ideology in cultural meaning of urban decline at the example of Detroit’s changed image, this article puts forth to debate in how far tourism shifts from being a leisure activity to being a marketing strategy and what that means for negotiations of cultural values through tourism semiotics, the significance of photography, and the visual in urban tourism, and eventually for the significance of tourism in urban development.