Aegean Sea islands, similar to other island regions around the globe, are determined by high quality wind and solar potential that stimulates the implementation of energy solutions based on renewable energy sources (RES). However, the current energy status suggests that RES penetration in the specific islands is limited in the order of 10%-15%, with oil-based power generation holding a dominant role. To this end, an advanced Microgrid Simulator has been developed in order to examine different energy strategies for island microgrids, considering both the option of stand-alone operation, as well as the option of interconnection to a host electricity system, which can be thought as equivalent of an electricity market.