Restrictions on greenhouse gas emissions and the existence of developing countries has diversified ship routes and ship types, making the ship operation more complex. Many types of simulation methods have come up in the last decade due to the enforcement of the energy efficiency design index. However, few studies that validated their simulations with actual data. This study performs the optimal ship routing of a 28,000-DWT-class bulk carrier to evaluate the optimal ship route with the speed loss analysis. The simulation results are compared with the measurement data of the bulk carrier in conditions including rough sea voyage in the Pacific Ocean. For comparison, a modified version of the speed loss analysis algorithm is developed. These algorithms are combined with the isochrone method. The differences in the simulation results with the American and European weather databases without higher wave avoidance and deliberate speed reduction are obvious. The simulated routes are closer to the measured ship trajectory if higher wave avoidance is considered. There are a couple of remarkable speed drops in the measured result, and the deliberate speed reduction is considered. Finally, some factors to control the reproducibility of ship routing including in rough sea voyages are summarized.