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The replacement of directly connected synchronous generators with power electronics interfaced generation has led to a decrease in system's inertia posing a significant challenge on frequency dynamics. In isolated systems with reduced inertia predefined limits for renewable penetration and primary reserves are frequently set for dynamic security purposes. This approach might not ensure dynamic security or can prove conservative in certain conditions. Furthermore, these approaches rarely consider the capabilities of inverter based renewable generation to provide frequency services. In this paper, a data driven approach, based on optimal classification trees is proposed to extract, from a detailed dynamic model of the system, the constraints for a frequency dynamic unit commitment formulation. Hence, both dynamic security and optimal exploitation of renewable and conventional units for power production and frequency support can be achieved. The advantages of the proposed method compared to conventional and state of the art approaches in frequency security are validated through dynamic simulations on a realistic model of Rhodes island and IEEE 118. Uncertainties in load demand and renewable generation are dealt by a robust optimization method. Its economic performance, computational overhead and modelling complexity is compared to a stochastic approach. [ABSTRACT FROM AUTHOR]