Skew superelevation has proven to be an efficient pavement constructional measure to address hydroplaning phenomena under specific critical superelevation runoff designs. However, this technique has raised concerns about user’s comfort when driving over the skewed edge of the pavement, especially for heavy vehicles and when the traveling speed is higher than the design speed. This paper aims to evaluate the driving comfort outcome on an improved skew superelevation design, where a rounding of the skew edge has been applied. This is achieved through the use of a simulation program which examines the vehicle and driver behavior when passing over it. The simulation program estimates many parameters including the lateral and vertical accelerations ( Gy and Gz) imposed on both elements, the vehicle and the driver. This evaluation is made for different alignment designs provided in the freeway design and for a broad range of especially high velocities ranging from 80 to 160 km/h (50–100 mph), as well as for different types of heavy vehicles. Also, the influence on the above parameters has been investigated in respect of the distance between two consecutive skew superelevations, concerning cases of entering and exiting a simple, low-length curve. The outcomes are classified in order to evaluate their variability as affected by each parameter change (speed, geometry, vehicle). Simulation results are compared with thresholds, as provided in the international literature, to ensure driver comfort and a high level of road safety.