As the Caribbean subregion seeks to implement strategies for meeting its obligations under the ParisAgreement, the sustainable development of its land transportation subsector has emerged as asignificant challenge. This relates to both the need to reduce green house gas emissions, for which thesubsector is a major emitter, as well as the necessity for reducing its overall dependence on importedfossil energy. While several policy initiatives have sought to address these issues, the evidence ofgrowing land transportation problems now motivates a closer examination of challenges in thesubsector. Among the main issues are increasing motor vehicle concentrations in small island spacesand growing traffic congestion arising from increased private motor vehicle ownership. All of thesefactors operate to produce economic, social and environmental burdens such as growing imports ofvehicles, fuel and spare parts; increased motor vehicle accidents and mortality; and socially deviantbehaviors such as road rage. Given the pivotal role of transportation in the advancement of economiesand society, this paper suggests policy options for improving land transportation efficiency andsustainability in the Caribbean. This study also seeks to add to the very limited literature related to the issue of land transportation in Small Island Developing States.