Maritime transportation and port management play essential roles in strengthening Indonesia's interisland connectivity, economic development, and territorial integration. However, the existence of a comprehensive maritime regulatory framework has not consistently ensured effective law enforcement or equitable access to transportation services. This study examined the effectiveness of maritime law enforcement and identified legal arrangements necessary to support equitable and sustainable transportation connectivity. A normative legal research method was employed using statutory and conceptual approaches. Primary, secondary, and tertiary legal materials, supplemented by supporting empirical data, were examined through qualitative juridical analysis. The findings indicated that Indonesia's maritime regulatory framework was generally aligned with relevant international legal instruments, although its implementation remained constrained by fragmented institutional coordination, uneven supervisory capacity, infrastructure disparities, and inconsistent regulatory compliance. The Sea Toll Program (Tol Laut) expanded from three routes serving 11 ports in 2015 to 39 routes serving 104 ports by August 2025, accompanied by reported reductions in regional price disparities. Nevertheless, variations in port dwelling times, continued dependence on government subsidies, and limited utilization of return cargo capacity remained significant challenges to logistics efficiency and the equitable distribution of economic benefits. These findings suggested that regulatory harmonization alone was insufficient to ensure effective maritime law enforcement and sustainable transportation connectivity. The study concluded that strengthening maritime governance required consistent regulatory enforcement, improved institutional coordination, integrated port and logistics infrastructure, and the incorporation of justice and sustainability principles into maritime transportation policies to promote equitable connectivity across Indonesia's archipelagic regions.