Maritime accidents remain a critical concern despite advancements in navigation technology and safety regulations. This paper examines maritime events over a 20-year period (2002–2021) using geostatistical analysis and GIS-based methods to identify key risk factors, trends, and high-risk zones. Analysis of the IMO’s Global Integrated Shipping Information System (GISIS) database highlights the influence of vessel type, flag state performance, accident timing, and geographical hotspots on incident frequency. Collisions, groundings, and fires/explosions are the most prevalent events, with aged vessels, open registries and outdated or incomplete hydrographic survey data posing significant risks. Poor flag state oversight, economic constraints, and human factors exacerbate maritime hazards. Although accident rates have declined, high-risk zones persist, necessitating stricter regulatory enforcement, fleet modernization, and improved accident reporting. Strengthening international collaboration and proactive risk management is crucial for ensuring safer global shipping operations, particularly in high-risk regions like the Caribbean Sea.