This study wants to give a contribution to the semi-automatic evaluation of rock mass discontinuities, orientation and spacing, as important parameters used in Engineering. In complex and inaccessible study areas, a traditional geological survey is hard to conduct, therefore, remote sensing techniques have proven to be a very useful tool for discontinuity analysis. However, critical expert judgment is necessary to make reliable analyses. For this reason, the open-source Python tool named DCS (Discontinuities Classification and Spacing) was developed to manage point cloud data. The tool is written in Python and is based on semi-supervised clustering. By this approach the users can: (a) estimate the number of discontinuity sets (here referred to as “clusters”) using the Error Sum of Squares (SSE) method and the K-means algorithm; (b) evaluate step by step the quality of the classification visualizing the stereonet and the scatterplot of dip vs. dip direction from the clustering; (c) supervise the clustering procedure through a manual initialization of centroids; (d) calculate the normal spacing. In contrast to other algorithms available in the literature, the DCS method does not require complex parameters as inputs for the classification and permits the users to supervise the procedure at each step. The DCS approach was tested on the steep coastal cliff of Ancona town (Italy), called the Cardeto–Passetto cliff, which is characterized by a complex fracturing and is largely affected by rockfall phenomena. The results of discontinuity orientation were validated with the field survey and compared with the ones of the FACETS plug-in of CloudCompare. In addition, the algorithm was tested and validated on regular surfaces of an anthropic wall located at the bottom of the cliff. Eventually, a kinematic analysis of rock slope stability was performed, discussing the advantages and limitations of the methods considered and making fundamental considerations on their use.