This work explores the relations between destination brands and predominant cultural trends in contemporary strategic communication and advertising. We face this objective by evaluating how a specific destination brand has responded in recent years to the main cultural trends with communication pieces by comparing two advertisements in two similar moments of 2021 and 2022. First, we discuss the concepts of place branding and destination brands and those of cultural trends to later articulate them with operational protocols on coolhunting, semiotics, the position of the observer, and the semiotic square. The result of this analysis proposal uses these tools for the in-depth study of each object and also to obtain significant links between objects, such as representations of places promoted for tourist consumption. Finally, we observe the elements that articulate current cultural trends with specific countermovements and the elements that are creatively and strategically combined to represent the destination brand through contemporary utopian links.