The objective of this research is to identify and quantify the sustainable impacts resulting from transportation investments at the port-city interface. These investments encompass two main components: 1) restoring the local inland waterway fairway for navigation, and 2) constructing a new railway bridge that traverses the primary waterway at the entrance of the seaport. The study is centered on the local transportation system in the northwestern region of Poland. Sustainability is assessed using an analytical tool derived from societal cost-benefit analysis and simulation in the relevant market transport performance in options with and without investment. Economic effects are evaluated in terms of savings in generalized transportation costs, which include transport operating expenses and travel durations. Environmental considerations encompass transport-related air pollution, greenhouse gas emissions, and well-to-tank emissions. Social aspects focus on issues like transport congestion, traffic noise, and transport-related accidents. Each type of investment yields distinct sustainable gains and distributes them among stakeholders differently. Additionally, the enhanced capacity of the rail bridge reveals the potential for a modal shift in the local passenger transport system, wherein passengers may transition from buses/cars to a fast railway. Tangible gains expressed in monetary terms allow for a sustainable assessment of transport investments. The elaborated research scheme can be employed to assess the sustainable ramifications arising from investments in intermodal transport at any port-city interface. It provides decision-makers with comprehensive insights into the economic, environmental, and social implications of various transport policies and interventions.