Shipping companies face the trilemma of investing in cheaper but more polluting conventional vessels, in more expensive but eco-friendly ones or postponing their investment. We quantify the price premium paid for eco-friendly vessels and investigate its determinants. The results indicate that eco vessels trade at an average premium of 25% compared to their conventional counterparts, while the corresponding income premia are between 9% and 15%. Our findings further suggest that the price premium depends on the market conditions, with income premia, past price premia, and fleet supply being strong drivers, while fuel costs and market liquidity have a less important effect. The magnitude and significance of these drivers vary based on the market state and segment. Overall, the paper documents the adverse effect that the current technological and regulatory uncertainty has on vessel investment and highlights the need for further policy intervention to reduce market uncertainty and encourage green investment.