© 2016 IEEE.The Greek state estimated a potential of 1,500 MW wind offshore capacity, which can be exploited by 2020, while 943.15 MW are located in the Northern Aegean Sea islanding region. This study presents a techno-economic assessment of wind offshore energy in the Northern Aegean Sea. Different topologies are proposed, taking into account wind offshore and islands interconnections using HVDC and HVAC technology. Investment indicators are based on the expected power generated by the Weibull wind speed probability density function and the total investment cost required for wind offshore engineering. The results show that the two wind offshore farms can secure the complete electrification of the neighboring islands and supply approximately 3,379 GWh to the main consumption centers in northern and central Greece on an annual basis. A sensitivity analysis towards investment optimization has been performed, proposing different wind turbine technologies and interconnection scenarios.