Road transportation worldwide is undergoing a rapid transition to more sustainable alternative fuel vehicle technologies as an effective means of dealing with climate change and related challenges. Several well-to-wheel studies have been done in mostly industrialized countries to assess the environmental impacts of these technologies as compared to conventional fuel vehicles. This study is a well-to-wheel assessment for the case of Lebanon and similar fuel-importing countries in the developing world where energy and transportation infrastructure are typically underdeveloped. The study considers the energy use, GHG and criteria pollutant emissions and economic costs for conventional and potentially feasible alternative fuel vehicle pathways for the Lebanese case in order to inform transition strategies to alternative fuels over the near, medium and long-terms. Results show that electric vehicles are beneficial for the long term as they require costly charging infrastructure and a clean electricity mix. Plug-in hybrid electric vehicles are attractive for the medium term, with gasoline or diesel hybrid electric vehicles the most feasible and beneficial technologies in the short-term. A sensitivity analysis showed that natural gas-based vehicles are competitive at high driving mileage, while locally produced biodiesel from waste cooking oil proved beneficial if emission controls are enforced.