Considering the complex dynamics, patterns, and particularities that peripheral and insular territories/regions present—e.g., as the fragility, they show to achieve a sustainable development and growth—a study that analyzes the land uses of this territories is seen as pivotal to identify barriers and opportunities for a long-term sustained development. Contextually, a general analysis was carried out through case study research methods covering those territorial typologies of the insular territory of Madeira Island, Portugal. The study, which was carried out through GIS mapping tools, enabled us to identify the land use changes in the last decades over the territory—allowing to establish a relation and identification of the associated barriers and opportunities presented by the territories to face the emerging sustainable development challenges. The study reveals the evident limitations of “ultra-peripheral” territories not only by the physical spatial dimensions but also by the difficulty to reconvert land uses. Thus, the main actors and their policies over the territory are even more relevant and need to be conducted in a more reasonable way—considering the fragility of this regions; such actions present higher impact over the territory and over their inhabitants’ life’s quality standards and finally on the long-term sustainability.