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The exponential grow of the wind sector in Portugal required the development of planning tools for the siting of the wind farms, its connection to the existing grid, as well as the assessment of the country's existing wind resource capable of enabling an economic, social and environmental sustainable development. The methodology developed and presented in this paper was initiated a decade ago with the classification of the existing wind data adequate to wind energy resource assessment as well as the identification of the constraints to the deployment of wind power plants. This GIS based methodology was systematically applied to the Portuguese territory and resulted on the identification of the available optimum sites for wind plant development at the lowest grid connection costs. The methodology may be easily applied to other countries or regions, thus enabling a systematic and objective approach to the wind power deployment.