Automated docking technologies of marine boats have been enlightened by an increasing number of literature. This paper contributes to the literature by proposing a mathematical framework that automates "trailer loading'' in the presence of wind disturbances, which is unexplored despite its importance for boat owners. The comprehensive pipeline of localization, system identification, and trajectory optimization is structured, along with techniques to enhance the reliability of performance. The performance of the proposed method was demonstrated with a commercial pontoon boat in Michigan, 2023. The results indicate the strong potential of the proposed pipeline, even in the presence of moderate wind disturbances.