The poor solubility of cannabinoids significantly limits their permeability, limiting their oral efficacy. Therefore, this study focused on the preparation of CBD and CBG delivery systems to improve their solubility and, consequently, assess increased penetration across biological membranes in the gastrointestinal tract. Mechanochemical methods such as milling, hot extrusion, co-precipitation in a supercritical carbon dioxide atmosphere, and electrospinning were used to prepare the tested cannabinoids. The identity of the prepared delivery systems was confirmed using XRPD, DSC, ATR-FT-IR, and SEM techniques. The chemical stability of the prepared cannabinoid delivery systems was assessed, and the physical stability of the resulting amorphous dispersions was monitored. Chromatographic techniques were used to assess changes in cannabinoid solubility in the prepared delivery systems. While using the PAMPA GIT model, changes in cannabinoid permeation across membranes simulating the walls of the gastrointestinal tract were assessed. The preparation of CBD and CBG delivery systems resulted in improved dissolution, which was coupled with improved membrane permeation. The system with the greatest potential for improving cannabinoid dissolution was identified as the amorphous solid dispersion obtained by co-precipitation of cannabinoids with selected solubilizers.