The Mediterranean island landscape is a mosaic of land-cover types that manifest the historical interaction between physical and anthropogenic processes that have affected significantly landscape composition and spatial configuration. The aim of this study is to investigate the processes and patterns of landscape changes in small Mediterranean islands as exemplified by the Aegean island of Sifnos, Greece. Satellite imagery was used to measure land-cover changes from 1987 to 1999. A suite of landscape metrics was employed to quantify changes in landscape structure. The results show that cropland suffered the highest area loss through conversions to semi-natural vegetation or settlements. The maquis vegetation of Juniperus phoenicea expanded over time with hotspots of expansion mainly located away from settlements. Overall, Sifnos' landscape became less fragmented and more homogeneous. The main drivers of landscape change were agricultural decline and tourism. These processes have resulted in semi-natural vegetation expansion and landscape closure. Landscape polarization of land-use intensity has increased with anthropogenic processes operating only on certain locations close to settlements and large parts of the island loosing their productivist profile. However, tourism should not be considered as the primary cause of land-use polarization but rather as an aggravating factor; agriculture and tourism do not represent competing economic sectors and land-use polarization is mainly the outcome of spatially co-occurring rather than spatially competing processes. Aegean island landscapes' management needs to be pragmatic and as such adaptable to future emerging priorities.