Using data acquired from NASA’s ASTER Level 1 Precision Terrain Corrected Registered At-Sensor Radiance (AST_L1T) product, this exercise uses remote sensing and geospatial tools and techniques to perform supervised land cover classification and change detection on the island of Barbados in the eastern Caribbean. Over a 15-year timestep between 2002 and 2017, the greatest absolute change in land cover detected is the area under agricultural production. Initially the dominant land cover type in the study zone, it has reduced by approximately two-thirds, and may well be in continual decline. This is juxtaposed against a high (relative) increase in infrastructure and related development on the landscape. Challenges with pervasive cloud cover across scenes and subsequent pre-processing rectification efforts affected robustness of results and thus reasonable caution is advised with specific data interpretation, but general trends in the direction and scale or magnitude of land cover change are considered substantive. Future research efforts could entail ground-truthing and dissecting the current classification scheme into more specific land cover identities.