The Anaklia Deep Sea Port represents one of the most ambitious infrastructure projects in Georgia and the South Caucasus, designed to serve as a strategic logistics hub along the Trans-Caspian International Transport Route (TITR), also known as the Middle Corridor. This paper evaluates Anaklia’s infrastructure readiness, with a particular focus on its rail and road integration, to assess its capacity to function as a competitive logistics node within Eurasian supply chains. Drawing on qualitative data from expert interviews, secondary sources, and empirical data from Georgia’s transport sector, the study identifies persistent bottlenecks in hinterland infrastructure, institutional coordination gaps, and operational inefficiencies at intermodal interfaces. While Anaklia is designed as a deep-water facility capable of handling Panamax vessels, its success depends on upgrading inland transport links and establishing coordinated governance mechanisms. The findings demonstrate that without strategic investments in rail modernisation, road bypasses, dry ports, and digital platforms, Anaklia risks becoming a maritime enclave rather than a regional gateway. The study also situates Anaklia within the broader debates on the Middle Corridor, highlighting both opportunities and limitations for its long-term viability. The paper concludes with recommendations for policymakers and practitioners, while acknowledging limitations related to data availability and project implementation timelines.