As one of the primary services ports provide, pilotage services aim to ensure the safe passage of vessels when entering and leaving the port. This study uses Taichung Port, located in the central part of the Taiwan Strait, as an example to analyze the impact of monsoon characteristics on wave conditions at pilot boarding points and to highlight their crucial role in safeguarding pilot boarding safety. By analyzing data from the ADCP (Acoustic Doppler Current Profiler) station north of the port’s northern breakwater and the Taichung buoy located southwest of the port, compare wave height distributions at the boarding point. The research addresses the impact of current and planned expansions, including constructing a new LNG receiving terminal with extended breakwaters, on wave dynamics and pilot operations. The study demonstrates that data from multiple sources—such as ADCP and buoy measurements—helps mitigate issues caused by missing data from specific stations. The analysis shows that numerical values differ slightly, while wave height trends at the boarding point are similar under current and expanded port conditions. The study concludes that the proposed expansion will likely affect wave diffraction patterns but will enhance the predictability and safety of boarding operations by reducing uncertainties associated with single measurement stations. Overall, the results of this study can enhance the understanding of marine meteorological information, improve the safety of pilot boarding operations, and thereby increase the efficiency and safety of port operations.