The assessment of agriculture at a regional scale is necessary to better guide regional agricultural planning. To improve the contribution of agriculture to sustainable regional development, assessments must take account of the locations and diversity of cropping systems. We have therefore developed a method based on a set of multi-scale indicators to assess the contribution of agriculture to the sustainable development of regions, and its evolution over time. This method can identify: i) sustainability issues, ii) relevant indicators that will provide information on impacts at the field scale, iii) a method to aggregate indicators, iv) data on cropping systems, and v) a database containing spatial units to analyse the whole region. Application of this method to Guadeloupe (2004-2010) enabled the definition of ten issues and 16 indicators, with three procedures to aggregate information from 36 cropping systems allocated to 11,908 fields between 2004 and 2010. Economic, social and environmental sustainability was poor in 2004, with high dependency on subsidies (47.3 M€.yr-1), low agricultural added value (48.5 M€.yr-1), low employment (only 1799 2 workers), significant risks of crop contamination and pressure on water quality. The total value of subsidies and the risks of river pollution tended to decrease between 2004 and 2010 because of a reduction in intensive banana cropping systems. In parallel, we were able to see that sugar cane, the most widespread crop in Guadeloupe, made only a small contribution to employment and food self-sufficiency during the studied period. The spatial representation revealed that improvements have been seen in southern Guadeloupe due to reductions in banana cultivation. This method was therefore helpful in identifying the most critical agricultural development issues and helping to highlight areas where relevant agricultural land use policies could be formulated.