Multibeam echosounders provide ideal data for the semi-automated seabed feature extraction and accurate morphometric measurements. In this study, bathymetric and raw backscatter data were initially used to manually delimit the reef morphologies found in an insular semi-enclosed gulf in the northern Aegean Sea (Gera Gulf, Lesvos Island, Greece). The complexity of this environment makes it an ideal area to “crash test” (test to the limit) and compare the results of the delineation methods. A large number of (more than 7000) small but prominent reefs were detected, which made manual mapping extremely time-consuming. Three semi-automated tools were also employed to map the reefs: the Benthic Terrain Modeler (BTM), Confined Morphologies Mapping (CoMMa), and eCognition Multiresolution Segmentation. BTM did not function properly with irregular reef footprints, but by modifying both the bathymetry and slope, the outcome was improved, producing accurate results that appeared to exceed the accuracy of manual mapping. CoMMa, a new GIS morphometric toolbox, was a “one-stop shop” that, besides generating satisfactory reef delineation results (i.e., detecting the same total reef area as the manual method), was also used to extract the morphometric characteristics of the polygons resulting from all the methods. Lastly, the Multiresolution Segmentation also gave satisfactory results with the highest precision. To compare the final maps with the distribution of the reefs, mapcurves were created to estimate the goodness-of-fit (GOF) with the Precision, Recall, and F1 Scores producing values higher than 0.78, suggesting a good detection accuracy for the semi-automated methods. The analysis reveals that the semi-automated methods provided more efficient results in comparison with the time-consuming manual mapping. Overall, for this case study, the modification of the bathymetry and slope enabled the results’ accuracy to be further enhanced. This study asserts that the use of semi-automated mapping is an effective method for delineating the geomorphometry of intricate relief and serves as a powerful tool for habitat mapping and decision-making.