Contemporary strategic planning represents a logic of space reproduction based on the promotion of tourism as the cornerstone of cultural and creative economy. However, some grassroots social initiatives aim to build alternative spaces to the economic approach that permeates contemporary urban planning. This article reflects comparatively on the cases of the Metelkova self-organized autonomous zone (Ljubljana, Slovenia) and the STOP Shopping Center (Porto, Portugal). We suggest that both the squatting of military installations (Slovenia), as the strategic reconfiguration of a private commercial building (Portugal), share common aspects that must be addressed under a place-making approach. In doing so, we propose that the cultural activity produced in these places, their socioeconomic influence in the urban environment and their ability to promote tourism has resulted in a brand that allows them to be tolerated by their respective local governments.