This chapter reflects on the relationship between urban complexity and flânerie. I analyse the controversial relationship established between the figure of the flâneur and that of the tourist. The concept of flâneur or flânerie is particularly suitable in highlighting some characteristics of late modernity as it is declined in a series of attitudes and behaviours, demonstrating that the very idea of flâneur must not be definitively consigned to the past but assumes a particular importance precisely in the current times. The first part provides a definition and historical reconstruction of the flâneur in the urban literature of the nineteenth century and of contemporaneity, up to the most recent sociological theories. The second part goes into the merits of the contradictions of the flâneur, an oxymoronic figure. The third part presents the distinctive and common characteristics between the flâneur and the tourist which are identified with respect to a continuum relating to three components: (1) the commercial component; (2) the experiential component; and (3) the existential component.