The purpose of this chapter is to understand the role of storytelling and social media on the engagement with the Historical Urban Landscapes (HUL) (UNESCO, 2011). Taking as a starting point the HUL approach, the framework is built around four key concepts: storytelling, heritage “from below”, co-presence, and lived experience. Our chapter contributes to the ongoing critical reflections on landscapes heritage-making processes through an innovative qualitative methodology combining digital ethnography, photography analysis, observation, and information gathering in situ (semi-structured interviews and institutional data) in Porto, Portugal. Results shed the light on areas where heritage boundaries are challenged and alternatives to the “authorised heritage discourses” (AHD) can be articulated and complementary, providing insights into everyday encounters with the urban landscape. Storytelling plays a significant role in the development of new touristic practices, combining urban walking, photography, and social media. The identified heritage attributes feature predominately affective, social and experiential values. It is believed that the outcomes can support heritage practitioners and policymakers to further the understanding for the diversity of heritage attributes and values and how to engage in a more inclusive way with Historic Urban Landscapes.