The Southern African Development Community (SADC) region is an economic community comprised of 16 countries in Southern Africa with a goal to achieve development, peace, security, and economic growth. Developing the regional freight transport system is essential for accomplishing these objectives. This paper investigates the potential of short sea shipping (SSS) in an African context, highlighting policy initiatives related to SSS development and identifying barriers and enablers of SSS to support international trade in the SADC region. According to our findings, SSS has the theoretical potential to work in the SADC given the large geographic region, projected freight volumes, and customs and trade policies the SADC region is pursuing. Such a system would have three main roles: to offer unimodal freight transport between port cities, to offer the main leg of an intermodal route, and to offer feeder services to deep sea shipping in a hub-and-spoke cycle. However, freight transport in the SADC region has a number of shortfalls that need to be addressed—of note, port competitiveness, customs provisions, and policies for intra-regional trade require impetus. Additional work is required in terms of policy to support SSS. Furthermore, considering the importance of synergies, the role of policy makers in improving trust, and developing cooperation among transport chain members needs to be explored.