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New technologies could be adequately introduced for an improved analysis aimed to the sustainable management and planning of the rural land, as well as its environment and landscape. Nowadays, this analysis is easier and more complete through the use of powerful and reliable tools. Several changes can be considered to be as models of territorial development, useful for an appropriate planning of the human interventions in a rural area. Remote sensing techniques could be employed for the monitoring of agricultural land variation, while Geographical Information Systems are excellent tools for landscape modeling and three-dimensional analysis. In this chapter, land-use changes in a rural area located in southern Italy were analyzed by comparing some historical cartographic supports with modern maps, in order to evaluate the morphological and vegetation variations of the agroforestry land during time. Moreover, a landscape analysis was conducted through the implementation of digital terrain models, which were enriched by draping land cover pictures over them. These elaborations finally enabled an evaluation in a scenic way of the aesthetic quality of the agroforestry landscape, allowing a virtual jump back to time periods when digital aerial photography was not yet even possible. This multi-temporal analysis with the support of GIS techniques revealed to have a great potential for assessing and managing landscape diversity and changes of vegetation, as well as for planning sound interventions over the landscape structures.