The maritime shipping industry plays a crucial role in economic development, particularly for archipelagic countries like Indonesia. However, investments in ship ownership are highly capital-intensive and exposed to volatility, making robust financial risk assessment essential. This study assesses the feasibility of investing in single-vessel ownership, specifically a Medium Range (MR) product tanker within a 12-year time frame, aligned with its remaining economic life, utilizing the Value at Risk (VaR) method in addition with Monte Carlo simulation to account for financial uncertainties. A Discounted Cash Flow (DCF) model assessed base-case feasibility using Net Present Value (NPV), Internal Rate of Return (IRR), and Debt Service Coverage Ratio (DSCR), and under deterministic conditions, the investment showed strong viability with an NPV of USD 13.50 million, IRR of 16.89%, and DSCR of 2.21. To assess risk, 10,000 Monte Carlo simulations were conducted, varying operating costs and dry docking costs at a 95% confidence level. The results demonstrate that even under combined risk scenarios, the project remains feasible, with an NPV at Risk of $12.18 million and an IRR at Risk of 15.47%. The research confirmed resilience under individual cost uncertainties, where modest reductions do not compromise feasibility, thereby demonstrating that MR tanker ownership is financially viable under both deterministic and probabilistic scenarios, and supporting VaR and Monte Carlo as practical tools for risk-informed maritime investment decisions.