This thesis aims to characterize the headland bypassing mechanism in a natural environment and investigate its variability relating it to the potential weather types and climate indices that influence the regional wave climate. The research is focused on Fingal Head (New South Wales, Australia), due to its natural cycles and relevance for regional coastal management. The analysis consists of three main stages: (1) describing the morphological variability updrift and downdrift of the headland, in different timescales through short-term topo-bathymetric surveys from 2018 to 2020 and long-term remote-sensing of shoreline and sandbar position from 1987 to 2020; (2) identifying the distinct atmospheric patterns and climate indices over the last decades associated with the main controlling factors of the sand bypassing in the study area and, (3) simulating headland bypassing events through numerical modelling in order to understand how the specific sea-state generated by the atmospheric systems leads to the triggering of a bypassing pulse. Results revealed that headland bypassing around Fingal Head is governed by two distinct processes controlled by the wave conditions and sediment availability. The sandbar-driven bypassing requires storm waves reaching the study area from southeast in order to trigger the sandbar-trough system formation around the headland while the sediment leaking process develops from similar wave direction approaching the coast but under lower wave heights. Strong low-pressure systems (e.g., Tropical Cyclones and East Coast Lows) positioned in the midlatitudes of the Coral-Tasman Sea basin were observed to generate the ideal sea-states for triggering a bypassing pulse around Fingal Head. The pulses triggered by this weather types have occurred at least 19 times in 33 years, which suggests 1 to 2 years cycles between bypassing events. The variability of the relevant weather types did not show a relationship with climate drivers; however, over a longer timescale (three to six years), cycles of accretion and erosion on the beaches adjacent to the headland have been observed to respond to the El Niño-Southern Oscillation and Pacific Decadal Oscillation. Hence, while the storm systems are responsible for triggering the pulse, it is the sediment availability that is the controlling factor of long-term cycles of bypassing. This understanding of the timescales of the headland bypassing process and its multiple driving forces is crucial to forecast future sediment budget variations and inform coastal management actions.