Agricultural landscapes of the Mediterranean Basin are home to unique and traditional productions, field elements, and cultivation practices. Despite their long-standing occurrence, these features have persisted within a highly dynamic context heavily influenced by changing agricultural profits, climatic anomalies, and a policy environment gradually embracing adaptive and mitigative approaches in what has been identified as one of the world’s fastest warming regions. Two primary, and contrasting, landscape change trajectories have been identified in the Mediterranean region, notably agricultural abandonment and intensification. While each trajectory brings opportunity, a number of adverse social-environmental impacts have likewise been documented. Unravelling the causal pathways behind these landscape transitions is crucial for the development of effective interventions aiming to minimize the likelihood of negative outcomes. Studies have however demonstrated that both trajectories share several driving forces, revealing the pivotal yet underexplored role and agency of farmers in shaping the landscape. This thesis implements a mixed-method and multi-scalar approach to explore possible futures for Mediterranean agricultural landscapes by investigating where and how adaptations may be implemented by farmers under changing conditions. This work is structured around two sub-national case studies, situated in Greece and Italy, as well as a continental-scale analysis, together capturing a diversity of landscape change realities occurring in the region. In the initial chapters, findings from field interviews with farmers and agricultural stakeholders within the two case study sites introduce two farming typologies characterizing the structural elements of farms, as well as the internal motivations guiding farmers in their decision-making. By means of spatial analysis and agent-based modelling, this thesis subsequently illustrates how the identified typologies are likely to influence the future implementation of adaptations at both the local and regional scales by responding to different institutional, socio-economic, and biophysical scenarios. In the last research chapter, the focus shifts from exploring the pathways via which adaptations may be enacted, to exploring where these may be implemented by mapping their suitability across the Mediterranean region. Together, the chapters presented in this thesis reveal an existing diversity of adaptation possibilities determined by heterogeneous farmer abilities, needs, attitudes, and values. This diversity holds implications for agricultural policy which has often upheld an intensification and modernization paradigm while overlooking diversified, smallholder realities and cross-sectoral policy coherence. Process of local participation and experimentation can thus be invaluable in the design of more targeted and needs-based policy instruments. Coupling these insights with a dynamic analysis of their respective social-ecological impacts can further contribute to anticipating maladaptive outcomes and vulnerability transfers – and may therefore help shape a fairer and more resilient future for the Mediterranean region.