This study explores a multiscalar approach that integrates Earth Observation (EO) and Geographic Information Systems (GIS) to support sustainable landscape planning. Using the Po River Basin in Northern Italy as a case study, we employed open-source satellite data to identify and analyze strategic areas for potential future landscape developments. By incorporating thematic layers such as vegetation indices, soil organic content, evapotranspiration and urban heat islands, we created detailed maps for large-scale regional assessments and micro-scale focus areas. The results highlight EO-based methodologies' potential to inform data-driven decision-making, facilitating site-specific interventions that enhance ecological connectivity, mitigate environmental degradation and optimize land use planning. This research emphasizes the potential role of EO in fostering sustainable territorial management and offers a replicable framework for future applications in urban and landscape planning.