Fixed-bottom foundations of offshore structures, mainly monopiles, are subject to extreme events and other critical cyclic nature loads. Since offshore wind turbine structures are slender, the manufacturers of offshore wind turbines give a range of frequencies for safe operation during a structure’s life cycle. Highly reliable measurements and accurate determination of shear moduli and damping ratios are crucial to ensure the stability of these structures, for example, to avoid the resonance of the structures. Because foundation–soil properties change over a period of time due to various environmental factors, this should be taken into consideration for designs. In the current investigation, behaviours of dry sand under dynamic loads were explored. Cyclic loads of strain amplitudes of 0.05%, 0.1%, 0.25% and 0.5% were carried out in a cyclic simple shear apparatus to explore the evolution trend of the stiffness and damping ratio of the soil. Attempts were made to simulate varying weather conditions by conducting cyclic tests with different strain amplitudes representing normal weather conditions and extreme weather conditions. It was found that soil dynamic properties vary remarkably at first and then tend to stabilise under cyclic loading with the same strain amplitude. However, with varying strain amplitude, property variations continue further. From numerical analyses using the discrete element method, it was found that this is due to the disturbance of soil, causing further particle rearrangements and soil compactions, following a sudden change of strain amplitude, which leads to further property variations.