The aim of this paper is to identify the potential benefits and obstacles of the interstate Short Sea Shipping (SSS) operation in the archipelagic Southeast Asia sub-region. Although literature has addressed a myriad of benefits and obstacles that were caused by the SSS operation as an alternative mode to unimodal land transport, it has been recognised that each SSS corridor may have its own peculiarities. Therefore, the identification of the potential benefits and obstacles through a Delphi survey among sub-regional expert respondents is expected to inform the countries of Southeast Asia on how to direct their limited resources to address the obstacles identified in order to enable a viable interstate SSS operation. The initial review of the benefits and obstacles of SSS operations will focus on case studies performed in Europe as the breadth of literature on SSS outside Europe is still limited. Hence, this study addresses the gap in the literature by focusing on SSS in archipelagic Southeast Asia particularly those involving interstate Ro-Ro operations and extending the usage of Delphi technique to the realm of interstate SSS.