Accurate predictions of wind and other weather phenomena are essential for making informed strategic and tactical decisions in sailing. Sailors worldwide utilize current state-of-the-art forecasts, yet such forecasts are often insufficient because they do not offer the high temporal and geographic resolution required by sailors. This paper examines wind forecasting in competitive sailing and demonstrates that traditional wind forecasts can be improved for sailing events by using an integration of traditional numerical modeling and machine learning (ML) methods. Our primary objective is to provide practical and more precise wind forecasts that will give sailors a competitive edge. As a case study, we demonstrate the capabilities of our proposed methods to improve wind forecasting at Lake Kinneret, a popular sailing site. The lake wind pattern is highly influenced by the area’s topographic features and is characterized by unique local and mesoscale phenomena at different times of the day. In this research, we simulate the Kinneret wind during the summers of 2015–2021 in up to one-kilometer resolution using the Weather Research and Forecasting (WRF) atmospheric model. The results are used as input for convolutional neural network (CNN) and multilayer perceptron (MLP) ML models to postprocess and improve the WRF model accuracy. These advanced ML models are trained using training datasets based on the WRF data as well as real data measured by the meteorological service, and subsequently, a validation process of the trained ML model is performed on unseen datasets against site-specific meteorological service observations. Through our experimental analysis, we demonstrate the limitations of the WRF model. It uncovers notable biases in wind direction and velocity, particularly a persistent northern bias in direction and an overestimation of wind strength. Despite its inherent limitations, this study demonstrates that the integration of ML models can potentially improve wind forecasting due to the remarkable prediction accuracy rate achieved by the CNN model, surpassing 95%, while achieving partial success for the MLP model. Furthermore, a successful CNN-based preliminary forecast was effectively generated, suggesting its potential contribution to the future development of a user-friendly tool for sailors.