Lisbon is a city of labyrinthine paths, due mostly to its irregular territory. The experiment of Flânerie in is explored in this paper through the identification of particular paths linked to the contemporary alternative cultural life, a debate being undertaken on how space and culture (alternative or dominant) mutually inspire one another. Urban and architectural elements will be analysed in connection with these paths, as well as the sensorial aspects of particular ambiences. Some attention is also given to accessibility, visibility and contrasts. The analysis of these aspects will lead us to explore the labyrinths and the entertainment that you can find in Lisbon’s streets, but also in inner spaces (alternative cultural places). These spaces tend to exist in the interstices of the city (wastelands), where urban exploration may happen thanks to its veiled character. One particularity of alternative cultural spaces is that they can both be visible and invisible, more or less accessible. Since they are spaces that suffered many transformations through time, by trying to adapt to different functions, their inner paths are often irregular and labyrinthine. This characteristic invites us to explore them and wander. Lisbon’s almost dramatic and quite poetic promenades have in fact a close relationship to its diverse cultural heritages and realities (fado, multiculturalism and contemporary alternative culture). Lisbon’s walls seem to speak poetry, but also to warn us about the general political and economic situation and complain about it. As if the city would talk to us while we take a promenade. Lisbon’s attractive scenography has become the perfect territory for managers and sponsors. Wouldn’t our urban experience become much less boring if adventure and “strong emotions” were constantly part of our routine? Fun and excitement in an urban form has already been tested and confined in Luna parks. But today the city streets are planned to be a place where leisure is permanently possible, urban landscape being invested in a ludic way (through interactive objects, irregular pavements, water jets in squares, colourful lights and materials). Graffiti is no longer illegal, but part of well-organized tourist tours, and alternative cultural places start to look more like a franchised entertainment centres than actually places for hosting underground culture. Labyrinths are now planned as part of the creative process of an architectural project in order to amuse users of coworking places. There’s no space left for hazard. Everything is created or manipulated in order to capture our attention and play with our senses. Urban exploration and dérive have now also become part of the dominant ideology, absorbed by this “new spirit of capitalism”. Nevertheless, the act of flâner cannot really be tamed. Its inherent praise of laziness and pleasure of being inutile goes against any attempt of control by productive work principles and market laws. May therefore flâner still manage to be a moment of introspection, and therefore of reflection and resistance?