This paper investigates the emerging autonomous aerial cableway technology to reduce the negative impacts of urban freight transportation. We focus on the infrastructure design problem to minimize the road-transportation externalities, taking pricing, investment costs, and the physical footprint into account. The network design problem is formulated as a mixed-integer linear programming (MILP) model that explicitly incorporates user participation constraints, ensuring that the resulting infrastructure configurations are consistent with the adoption behavior of freight service users. The proposed framework is evaluated through a case study conducted in the Historic Peninsula of Istanbul, one of the world’s most prominent historic and touristic urban regions. To realistically capture user adoption behavior, we conduct a stated-preference experiment with more than 200 store owners operating in the study area and estimate a utility-based adoption model that reflects their sensitivity to service attributes and pricing. Our results demonstrate that the proposed aerial cableway system can substantially reduce the environmental and operational costs associated with conventional road-based freight transportation while maintaining economically viable operations. In particular, the findings show that the network design and its environmental performance are highly robust to pricing, remaining stable across a tenfold range of service fees (1–10 TRY/kg), and that public subsidies yield negligible additional benefit once a cost-reflective price is in place. Emission reductions of up to 80% can be achieved without external subsidies, requiring only modest service fees from participating businesses. Full decarbonisation of ground freight transfers remains feasible within the same moderate price range, though it becomes infeasible when prices exceed a critical threshold, highlighting the importance of careful tariff design. The study highlights the potential of autonomous aerial freight systems as a financially self-sustaining and environmentally effective logistics alternative for dense urban environments facing congestion and infrastructure limitations.