Mediterranean land systems are amongst the most susceptible to global change, in part due to the region’s vulnerability to climate change and misfit within a high production demanding political and societal setting. The impact of global drivers at a local scale (i.e., the possible trajectories of change of a territory) are context-dependent, and to some extent dependent on how local actors perceive them and act upon them. In this study, we focused on southeast Portugal and conducted 22 interviews and 1 collective workshop to understand how different actors across the territory anticipate the development of the region and its land systems. From our results, we get a picture of a depopulated territory, constrained by ill-adjusted policies to its harsh conditions, including little water availability and continuous depopulation. We found contrasting preferred trajectories of development for the territory. On one hand, there is a preference for prioritizing traditional land systems, usually rainfed and multifunctional. Contrasting, a need for water reservoirs that would increase water availability and allow for profitable agricultural activities and thus fixate population is recognized. The different perspectives fit with a wider debate on the role of agriculture, intensification and ecosystem services under an increasingly arid Mediterranean. The next challenge is to integrate technical expertise and knowledge with local needs and initiatives, to fit in a broader scale strategic plan. We identify a lack of technical support regarding soil health. Poor soil, from the perspective of several stakeholders, is a characteristic of the region. Knowledge dissemination is urgent so that farmers can proactively improve soil health and benefit from its capacity to increase production and retain water. We urge a higher effort from the scientific community focusing on marginal areas, supporting knowledge dissemination and analysis of the impacts of different trajectories of development.