The marine surface wind field (10 m) over the Greek seas is analyzed in this study using The RegCM. The model’s spatial resolution is dynamically downscaled to 10 km × 10 km, in order to simulate more efficiently the complex coastlines and the numerous islands of Greece. Wind data for the 1980–2000 and 2080–2100 periods are produced and evaluated against real observational data from 15 island and coastal meteorological stations in order to assess the model’s ability to reproduce the main characteristics of the surface wind fields. RegCM model shows a higher simulating skill to project seasonal wind speeds and direction during summer and the lowest simulating skill in the cold period of the year. Extreme wind speed thresholds were estimated using percentiles indices and three Peak Over Threshold (POT) techniques. The mean threshold values of the three POT methods are used to examine the inter-annual distribution of extreme winds in the study region. The highest thresholds were observed in three poles; the northeast, the southeast, and the southwest of Aegean Sea. Future changes in extreme speeds show a general increase in the Aegean Sea, while lower thresholds are expected in the Ionian Sea. Return levels for periods of 20, 50, 100, and 200 years are estimated.