The increasing availability of high-quality digital elevation models (DEMs) has been associated with a growing interest in developing quantitative analyses aimed at taking advantage of these detailed, updated, and promising digital datasets. Land-surface quantitative (LSQ) analysis is valuable for describing the land-surface topography and performing measures of the signature of specific geomorphic processes, taking into account site-specific geological contexts and morphoclimatic settings, proving to be particularly effective in transitional environments, such as rocky coasts. This paper presents the results of research aimed at investigating the spatial distribution of gravitational landforms along rocky coasts, by means of LSQ analysis based on a DEM with a ground resolution of 2 m, derived from airborne LiDAR (light detection and ranging) surveys. The study area is at Mt. San Bartolo (Northern Marche, Italy) and characterized by a sea cliff diffusely affected by gravitational phenomena of different sizes and types. Geomorphological and geological field data, interpretations of remotely sensed datasets derived from ad hoc unmanned aerial vehicle (UAV) flights, and DEM-derived hillshades were also adapted to support LSQ analysis. In detail, four morphometric variables (slope, roughness, terrain ruggedness index, and elevation standard deviation) were computed and the outputs evaluated based on visual–spatial inspections of derived raster datasets, descriptive statistics, and joint comparison. Results reveal the best performing variables and how combined interpretations can support the identification and mapping of zones characterized by varying spatial distribution of gravitational landforms of different types. The findings achieved along the Mt. San Bartolo rocky coast confirm that an approach based on land-surface quantitative analysis can act as a proxy to efficiently investigate gravitational slope processes in coastal areas, especially those that are difficult to reach with traditional field surveys.