Accurate prediction of drifting trajectories is essential for improving the operational efficiency of maritime search and rescue (SAR), particularly within the complex geomorphological settings of island and reef regions, such as those in the South China Sea. This study investigates the drift characteristics of life rafts under varying loading conditions across both open-sea and island–reef regions. Comprehensive field experiments were conducted over 15 days in the waters around the Wanshan Archipelago, using advanced instruments to collect wind, current, and drift trajectory data. Based on these observations, two models—the AP98 leeway model and a BP neural network model—were developed and validated. The results show that the AP98 model performs better in open-sea conditions, whereas the BP neural network provides more accurate predictions in island and reef areas with complex environmental factors. A Monte Carlo simulation was also integrated to enhance the robustness of drift area predictions. These findings offer valuable insights into life raft drift behavior in complex marine environments and provide technical support for improving SAR operations in island–reef regions.