Climate change and aging infrastructure have elevated the importance and role of resilience for transport infrastructure. This research paper introduces a robust risk analysis tool, specifically designed to improve the benefit of investments in infrastructure resilience, particularly in the context of road transportation networks vulnerable to floods. The HAzard & Risk Multiregional Assessment tool (HARMA), integrates multiple modeling perspectives and exploits a wide variety of data sources to evaluate both the direct and the indirect cost of hazard-induced damages and disruption to the transport network. Key features of the tool include its ability to quantify the likelihood and severity of identified hazards, locate the exposed assets and links of the network, assess the extent of damages, and evaluate the socio-economic impact due to the disruption of transportation activities. Additionally, the tool facilitates scenario analysis, enabling decision-makers to explore different risk mitigation strategies, optimize interventions, and prioritize investments for enhanced resilience under varying budget constraints. One of the key strengths of the tool is its global applicability even in data-poor environments, while not limiting users from inputting region-specific data if available. This study offers a practical application of HARMA in the region of Thessaly, Greece, which has been the hot-spot of major, destructive floods in the recent past, after storm Daniel (2023) and Medicane Ianos (2020).