Currently, no guidelines cover use of pesticides in the forested areas of the Canary island of Tenerife. An index-based model (Li) was used to rank the leaching potential of 50 pesticides that are, or could be, used for management purposes in the pine forest areas of Tenerife. Once the pesticides with the greatest leaching potential were identified, regional-scale groundwater vulnerability assessments, with consideration for data uncertainties, were generated using soil, climatic, and chemical information in a geographic information system framework for all pine forest areas of the island. Process-based simulations with the pesticide root zone model for the areas and pesticides of highest vulnerability were conducted to quantitatively characterize the leaching potentials. Carbofuran, hexazinone, picloram, tebuthiuron, and triclopyr were each identified as being potential leachers.