Wind energy and photovoltaic solar energy (PV) are the most mature renewable energy technologies and are widely used to increase renewable energy penetration in non-interconnected Greek islands. However, their penetration is restricted due to technical issues related to the safe operation of autonomous power systems, the current conventional power infrastructure and their variable power output. In this framework, renewable energy curtailment is sometimes a necessity to ensure the balance between demand and supply. The ability of autonomous power systems to absorb wind and PV power is related to the load demand profile, the type and the flexibility of conventional power plants, the size of power system and the spatial dispersion of wind farms. In this connection, a probabilistic approach for estimating wind energy curtailment is thoroughly applied in most of the autonomous power systems in Greece, using detailed information about load demand and conventional power supply. In parallel, high resolution mesoscale model-based hourly wind data for typical meteorological wind year are used to represent the wind features in all the sites of interest. Technical constraints imposed by the local power system operator, related to the commitment of conventional power plants and the load dispatch strategies are taken into account to maximize renewable energy penetration levels. Finally, application for wide ranges of wind and PV capacity and the thorough analysis of the parameters leads to the presentation of comparable results and conclusions, which could be widely used to predict wind energy curtailment in non-interconnected power systems.