This paper compares two headland sand bypassing, one natural and one artificial. Both areas are located at similar latitudes but distant longitudes: 1) southern Gold Coast (28.15ºS, 153.5ºE), where an artificial, headland sand bypassing system has been operating since 2001 and is set to simulate the natural sand transport and 2) the north shore of Santa Catarina State, southern Brazil (27.4º S, 48.5º W), where the headland bypassing process occurs naturally. For Santa Catarina North Shore, a numerical model was created, calibrated and validated. Furthermore, the sand transport equation that best describes the process were tested against measured data. Finally, 26 scenarios of tides, winds and waves were simulated individually in order to assess the importance of the contribution of each driving force to the process. The Gold Coast data was derived from the literature. The Santa Catarina North Shore results showed that while waves are the main driving force for the process. However, the different magnitudes of sand transport between the two areas are related to: 1) differences in wave climate; 2) angle of wave approach with more oblique waves resulting in higher sand transport rates; 3) and the extent of headlands – the Santa Catarina Island North Shore presented headlands at the exposed area extending offshore between 500 to 1,300 m while on the Gold Coast, Point Danger and the Tweed River training walls extend about 100 and 200 m offshore, respectively.