Mine hoists operate in confined shafts that are also used as ventilation ways, where the movement of conveyances at relatively high velocities may disturb local airflow conditions and generate aerodynamic forces. The shape of the conveyance may significantly affect the resistance generated during operation, particularly when the conveyance moves within the limited cross-section of a mine shaft. In this study, the influence of conveyance geometry on the aerodynamic characteristics of a simplified hoisting system was investigated. Initial theoretical considerations were conducted to estimate the expected range of aerodynamic drag and to support the interpretation of subsequent experimental and modeling results. Experimental tests were then conducted using scaled models in a wind tunnel. Several geometric configurations were analyzed and compared in terms of the generated drag force. A computational model of the investigated system was also developed to support the experimental campaign and provide insight into the flow phenomena occurring between the conveyance and the counterweight. The simulations enabled qualitative analysis of velocity distributions and flow structures within the shaft domain.