Multi-stakeholder perceptions of landscape changes are increasingly recognized as essential inputs to discussions on future landscape developments, particularly when addressing the future of European rural areas experiencing agricultural abandonment. This research presents a case exploration of abandonment of olive plantations in east Lesvos, Greece. We conducted two sets of semi-structured interviews to relate an exploration on local farmers’ ability and willingness to maintain the plantations, to the results of a landscape preference survey undertaken with tourists. Three farmer types are identified following a cluster analysis based on attributes of individual ability and willingness to farm. Farmers belonging to the prevalent type revealed low ability and willingness and expect to further extensify their farms. The remaining two farmer types have higher willingness; they are motivated by cultural reasons, more frequently expressing a desire to maintain their land under family ownership, and partake in social cooperative initiatives promoting practices valorizing the olive plantations. We outline how these types interact with regional drivers of change, and partly also contribute to persistence of abandonment through constrained ability to farm. Abandonment does not align with current landscape preferences of tourists, who favor cultivated landscapes, elements of traditionality within built infrastructure and undertake nature-based activities. We discuss how high willingness to farm associated with professional and pluri-active forms of farming may however provide opportunities to maintain the cultivated landscape and synergize with (agri-)tourism demand. Our findings are comparable to those of other European studies, contributing to discussions on the future of its rural landscapes.