This study investigated the possibility of using short sea shipping (SSS) as a sustainable freight modal alternative by analyzing data collected from shippers in the New York State Capital Region. To this end, qualitative and quantitative approaches were jointly used. The qualitative analysis focused on exploring in-depth interviews with the decision makers regarding the drivers and the barriers to firms shifting to SSS. The quantitative efforts included estimating discrete choice (ordinal logit) models to assess the influence of four key governing aspects (leadership buy-in, emergency logistics, public policy, and sustainability) on the probabilities of shifting to SSS supported by the findings from the qualitative part. This paper also includes a comprehensive description of various variables, factors influencing the current mode choice, shippers’ perceptions, and willingness to use SSS. The results showed that firms with higher truck shares had fewer chances to switch to SSS unless in emergencies. Unfortunately, sustainability was the least valued by most of the participants in choosing SSS. Hence, lower costs and better service were essential. The ordinal logit models provide a potential tool for policymakers and freight planners to estimate the probability of firms choosing SSS over the current mode.