Remote Sensing (RS) and Geographic Information Science (GIS) techniques are powerful tools for spatial data collection, analysis, management, and digitization within cultural heritage frameworks. Despite their capabilities, challenges remain in automating data semantic classification for conservation purposes. To address this, leveraging airborne Light Detection And Ranging (LiDAR) point clouds, complex spatial analyses, and automated data structuring is crucial for supporting heritage preservation and knowledge processes. In this context, the present contribution investigates the latest Artificial Intelligence (AI) technologies for automating existing LiDAR data structuring, focusing on the case study of Sardinia coastlines. Moreover, the study preliminary addresses automation challenges in the perspective of historical defensive landscapes mapping. Since historical defensive architectures and landscapes are characterized by several challenging complexities—including their association with dark periods in recent history and chronological stratification—their digitization and preservation are highly multidisciplinary issues. This research aims to improve data structuring automation in these large heritage contexts with a multiscale approach by applying Machine Learning (ML) techniques to low-scale 3D Airborne Laser Scanning (ALS) point clouds. The study thus develops a predictive Deep Learning Model (DLM) for the semantic segmentation of sparse point clouds (<10 pts/m2), adaptable to large landscape heritage contexts and heterogeneous data scales. Additionally, a preliminary investigation into object-detection methods has been conducted to map specific fortification artifacts efficiently.