This WorkShop, chaired by Dr. Apostolos Papakonstantinou and delivered by Dr. Athos Agapiou, explores the integration of Earth Observation (EO) and geospatial technologies for cultural heritage mapping and monitoring. Organized under the COASTLINE Project in collaboration with MDPI’s Remote Sensing journal, the webinar highlights the evolution of remote sensing applications, tracing its roots from early balloon-based aerial photography of Stonehenge in 1906 to modern multi-sensor, multi-temporal satellite data analysis. A meta-analysis of Scopus literature demonstrates a sharp rise in academic publications since 2000, driven by key advancements in 3D modeling, UAVs, LiDAR, structure-from-motion, and deep learning algorithms. The core applications focus on two main areas: underground site detection and site monitoring. For subsurface detection, physical-based radiative transfer models (such as PROSAIL) help researchers generate synthetic spectral signatures to understand crop mark formations caused by buried archaeological structures. Regarding heritage monitoring, satellite platforms—particularly the European Union’s Copernicus program (Sentinel-1 and Sentinel-2)—provide critical data for tracking urban sprawl around ancient sites like Paphos, assessing damage after events like the 2020 Beirut explosion, identifying looting activities, and evaluating natural hazards such as earthquakes and thermal conditions in historic centers. Additionally, the presentation details specialized infrastructure projects, including CONNECTING, ENGINEER, and ARGUS. These initiatives employ high-precision equipment—such as full-frame mapping cameras, airborne LiDAR sensors, hyperspectral drones, and underwater ROVs—to build robust preservation workflows. Ultimately, the authors emphasize the need to bridge the gap between space technology experts and end-users, such as policymakers and heritage managers. While Copernicus services currently meet a portion of user demands, enhanced awareness, capacity building, and tailored data integration remain vital to fully leverage remote sensing for safeguarding global cultural heritage.