The concurring forces of agricultural intensification and abandonment have been identified as some of the more prominent and polarizing drivers of landscape change in Europe. These transitions may induce deterioration in landscape functioning and character, particularly in cultural landscapes demonstrative of evolving human-environment dynamics having sustained multiple environmental benefits through time. Cultural and behavioral motives are significant root influences to such landscape transitions, yet efforts to address landscape degradation are often hampered by a failure to account for the heterogeneous decisionmaking nature of its agents of change and the inherent complexity of socio-ecological systems. Novel techniques are required to further disentangle responses to multi-level drivers and discuss alternative landscape development trajectories. Agent-based models constructed by means of participatory approaches present increasingly applied tools in this context. This study sought to capture and model the future perspectives emerging from presently occurring farming discourses in the region of Gera (Lesvos, Greece), characterized by persistent abandonment of its traditionally managed olive plantations. We constructed an agent-based model iteratively in collaboration with the local farming community and experts in landscape research. Empirical findings informed the model through the construction of a farmer typology, revealing a heavy reliance of the farming community upon sectorial profitability, prevalent cultural farming motives and emerging landscape initiatives. The model examined the de-coupled role of agricultural profitability and landscapes initiatives in shaping the behavior of land managers, mapping alternative landscape futures over a period of 25 years. Model results illustrate increased profitability alongside action by landscape initiatives alone can reverse abandonment trends within the simulated time frame. The hypothesized ability of landscape initiatives to maintain and promote a cultural drive amongst adhering farmers is crucial for securing behavioral transformations towards professionalism. This study confirmed agent-based modelling to be intuitively received by stakeholders who significantly contributed to model structure refinement and the rejection of a status quo scenario.