The high cost and environmental impact of fossil-fuel energy generation in remote regions can make renewable energy applications more competitive than business-as-usual scenarios. Furthermore, energy and transport are two of the main sectors that significantly contribute to global greenhouse gas emissions. This paper focuses on the generation of thermal energy and the transport sector of a fossil fuel-based energy independent island in Greece. We evaluate (1) technologies for fully renewable thermal energy generation using building-specific solar thermal systems and (2) the replacement of the vehicle fleet of the island with electric and hydrogen-fueled vehicles. The analysis, based on economic and environmental criteria, shows that although solar thermal decreases greenhouse gases by 83%, when compared to the current diesel-based situation, it only becomes economically attractive with subsidy scenarios equal to or higher than 50%. However, in the transport sector, the sum of fuel and maintenance costs of fuel-cell and electric vehicles is found to be 45% lower than that of the current fleet, due to their approximately seven times lower fuel cost. Lastly, it will take approximately six years of use of the new vehicles to balance out the emissions of their manufacturing phase.