The Caribbean and Puerto Rico are lagging in ramping renewable energy (RE) capacities. Energy system transition pathways reaching 100% RE by 2050 for Puerto Rico and the Caribbean are analyzed for all energy supplies. Islands are often limited in available land; therefore, scenario variations are considered, including offshore floating photovoltaics (PV). The results for Puerto Rico clearly indicate the enormous benefits of reaching 100% RE, as the levelized cost of electricity (LCOE) can be reduced from more than 100 €/MWh in 2020 to 47.4 €/MWh in 2050, and the levelized cost of energy, including all energy sectors, declines from 79 to 53 €/MWh, respectively. PV reaches 81% of all electricity supply, leading to 33.4 GW installed capacity, thereof 17.5 GW offshore floating PV due to area limitation. Without area limitation, the total system cost would be about 2.7% lower. The key metrics for the Caribbean development from 2020 to 2050 are as follows: electricity generation from 110 to 677 TWh, PV supply share from 2% to 92%, PV capacity from 1 to 332 GW, thereof 19% prosumer, 81% utility-scale with up to 38% offshore floating PV, and LCOE from above 100 to 31.9 €/MWh. The prosperity of Puerto Rico and the Caribbean is closely related to solar PV, the dominating source of energy in their Solar-to-X Economy.