This study evaluated the possibilities of energy transition in Cuba 2030. Cuba is currently in a vulnerable energy situation since it strongly depends on the importation of fossil energy. Strategies based on intermittent RES (solar and wind) can reduce this vulnerability, but the introduction of this type of source impacts the energy system's characteristics and aspects at a country/regional scale. Most of the studies about energy transition strategies focus on the evaluation of a few specific arbitrary scenarios or the classic economic optimization approach. This research relies on existing methods to evaluate energy scenarios. However, some aspects of our approach are original: differently to the comparison of arbitrary scenarios we evaluate a fairly large number of scenarios, and differently to the classic optimization we consider many different indicators (e.g., energy security, carbon footprint, air quality, and economic). This allows the description of the trends of the changes in the energy system and the evaluation of the benefits linked to a progressive introduction of intermittent sources. Scenarios for Cuba correspond to a progressive introduction of intermittent sources to reduce fossil fuel importation. These scenarios were compared with the official projection of the Cuban government for 2030 showing that the introduction of solar and wind improve the situation of the island by reducing CO2 emissions, improving air quality, and generating economic benefits. Monetizing the CO2 emissions results in greater economic benefits through carbon compensation. Furthermore, replacing Internal Combustion Vehicles (ICVs) with Electric Vehicles (EVs) could offer additional benefits across all these aspects.