Increased wind energy penetration influences the power system dynamic response to transient disturbances. Replacement of conventional production units with converter-connected wind turbines reduces natural power system inertia contained in rotational masses of synchronously connected turbine-generator units, therefore creating low-inertia power systems. Such a transition has an adverse effect on system resilience to disturbances and on the capability to maintain stable operation. This research examines the impact of high regional wind power production on system transient stability in the case of island operation of the Croatian power system. The system is divided into four geographical areas modeled as four centers of inertia with aggregated parameters. The study investigated initial transient RoCoF values in different areas for current and future wind capacity share scenarios, loading data, and primary frequency regulation settings. The modeling and scenario analysis have been performed on a detailed phasor power system model in the MATLAB/Simulink environment.