The maritime industry is addressing environmental issues, and “cold ironing” offers a promising solution. This method involves supplying ships at port with energy, reducing fossil fuel dependence and emissions, and aiding in global climate change efforts. It is especially important for islands like Lesvos, which suffer from high energy costs and environmental issues due to imported fossil fuel reliance. However, research gaps exist in using renewable energy sources (RES) for cold ironing, mainly due to insufficient data on power needs and lack of monitoring for precise calculations and the very limited applications for the case of non-interconnected islands. This study uses real data from the port of Lesvos to evaluate power requirements for cold ironing and assesses the viability of a wind power park for an electrified port with the novelty and uniqueness of developing the application on a non-interconnected island. It also examines potential CO2 emission reductions. Data from Marine Traffic S.A. were used, considering factors like ship arrivals, hoteling duration, and engine types. This study also includes a simulation using RETScreen software for a 20 MW wind park intended for port operations. The findings show that the monthly energy demand at Mytilene port is around 6118 MWh, with an average power demand of 8.2 MW. The simulated wind park could supply about 72,080 MWh yearly, with a significant surplus (14,956 MWh annually) exportable to the grid. However, demand fluctuations mean the port might need an extra 924 MWh from the main grid. This underscores the need for additional strategies like energy storage and demand–response practices to fully transition to 100% RES-powered operations.