Islands as peripheral and ultra-peripheral are typically highlighted as ecologically sensitive areas to human activities due to the tremendous biological diversity of beings and the future possibility of habitat loss. In this regard, the comprehension of the land occupation dynamics and trends in the ultra-peripheral territories is crucial to attempt long-lasting regional sustainability, as is the island region’s case. Therefore, the present article aims to analyze the trends and dynamics of the land-use changes on the European Archipelagos of the Macaronesia Region over the last three decades, using the CORINE (Coordination of Information on the Environment) data. Some of the obtained results show that about 3.4% of the Azores’ surface is characterized mainly by discontinuous urban fabric, representing 67% of the total urban fabric of the Azores over the last thirty years. Additionally, in Madeira Archipelago, the land is mainly occupied by forest and semi-natural areas, representing almost three-thirds of the territory. A similar scenario is verified in the Canary Islands, where forests and semi-natural areas represent approximately three-quarters of the territory. Once more, this study shows the relevance of the island areas’ unique character, which should be preserved and protected. Therefore, the priorities must be defined and established management strategies that are significant for the well-being of these highly valued areas. Moreover, the study showed that notable changes had occurred in the period 1990–2018 in this landscape. Hence there is a need for appropriate measures to mitigate these negative impacts on the environment.