Literature has focused on studying port choice independently or as an element of a supply chain without considering the joint selection with the country of origin/destination of the imports/exports. However, the characteristics and location of a port may make it more attractive to mobilize more freight from/to some particular countries rather than others, making the port choice decision dependent on the country of origin/destination of the cargo. This article proposes advanced econometric models to evaluate simultaneously port choice and the country of origin/destination choice for Colombian imports and exports. Findings suggest that for imports and exports domestic freight rate is the most important variable for the joint choice process. Also, for exports, maritime transit time is more relevant than for imports, while for the frequency of shipping lines the opposite is true. The existence of a trade agreement and the gross domestic product per capita also have a significant influence on the election of a country for exports/imports.