Land–sea interaction dynamics are physiologically regulated by an exchange of matter (and energy) between the anthropic system and the natural environment. Therefore, the appropriate management of land–sea interaction (LSI)contexts should base on those planning approaches which can holistically support coastal development, such as Maritime Spatial Planning (MSP) and Climate Adaptation Planning (CAP). One of the main limiting factors for this integration is the fragmentation of existing databases and information sources, which compose the territorial knowledge framework. Investigations have sought to address the representation and assessment of “wicked” and interconnected coastal problems. The present research focuses on the production of the necessary information to fill sectorial knowledge gaps and to merge the available data into a single framework. The research methodology is based on remote sensing assessment techniques and is designed to be replicated in other coastal areas to integrate CAP and MSP. The output maps are a result of the empirical application of the integration of the assessment techniques and are meant to support local decision-making processes. The result aims at illustrating and highlighting the relationships between climate change impact vulnerabilities their spatial relation to marine resources and maritime activities. This can support effective actions aimed at environmental and urban protection, the organization of the uses of the sea and adaptation to climate impacts. The application of the assessment techniques is developed on a case study in the north Adriatic Basin. The Gulf of Trieste constitutes a representative case study for the Mediterranean Basin due to its transboundary nature. The relationship and the ongoing projects between Slovenia and Italy make the case study an interesting context in which to test and train the proposed integrated planning approach. Therefore, the study investigates local vulnerability to climate impacts, i.e., Urban Heat Island (UHI) and urban runoff, and the existing relationship between the urban fabrics and the marine environment.