While there is general consensus on the importance of landscape perception in urban studies, there is still a need to broaden the toolkit for researchers and practitioners to document, analyse and interpret these inputs, in line with the postulates of the European Landscape Convention and overcoming conventional formats based on descriptions and static photography. This becomes particularly pertinent in the peri-urban landscapes of large cities, bearers of the relations and contradictions between urban growth, resource consumption and landscape protection, and especially vulnerable to tabula rasa approaches. We case study the surrounding landscapes of Madrid at a metropolitan scale, addressing the gap between scopes and scales of recent landscape reports and focusing on two elements connecting (visually, or physically) the city with its commuting zone: lookouts and roads. An expert-based methodology presents the criteria for their selection and a description of desk and field work. A sample for each local approach is further developed to exemplify the application, combining cartography, 3D modelling, visual basins, on-site photography and interpretive drawings. This results in a multifaceted vision of how the city and its hinterland is perceived, illustrating both outstanding and everyday landscapes and how they interweave in a continuous experience.