This paper presents a study carried out to first assess the impact of the Panama Canal expansion (PCE) on selected Caribbean ports, and thereafter, to examine how the ports can adapt in order to seize new opportunities created by the expansion. An applied case of long-term dynamic planning and flexibility in engineering design is presented for a new port terminal in Barranquilla, Colombia. Furthermore, this paper presents the results of a stochastic method for quantifying opportunities from containerized traffic using dynamic forecasting, real options analysis, and Monte Carlo simulation, within the framework and spirit of adaptive port planning under uncertainty.