Land degradation involves a wide array of natural and human induced factors that affect agricultural productivity. These factors can exist in various non-unique and complex combinations of different environmental settings, often making detection and monitoring of the phenomenon a difficult undertaking. As a result, no universal approach exists for the assessment of land degradation. In order to be efficiently and effectively managed, this phenomenon should be assessed and quantified in a systematic manner so as to identify the causes, processes and factors leading to degradation nationwide. This study attempts to assess the vulnerability of watersheds to land degradation island-wide, based on the use of Geoinformatics tools to combine in situ and satellite-derived information on existing degraded areas in Trinidad. Nine biophysical attributes were considered; six from in situ measurements (i.e. soil type, soil texture, soil drainage, erosion status, geology and land capability) and three derived from satellite data (i.e. elevation, slope and NDVI). Specific values for these attributes were taken at degraded sites and generalized to watersheds, and then assessed using multi-criteria analysis. Results obtained by the developed methodology showed good agreement with existing knowledge on land degradation in Trinidad, especially for the North Western part of the island. They also showed that soil drainage and erosion status were found not to be affecting factors of land degradation at the watershed scale. This approach can be adopted as a simple and objective way of assessing land degradation vulnerability, supporting more detailed analysis in data-sparse regions.