The volume of a 40 ft container is twice as large as that of a 20 ft container. However, the handling cost (loading, unloading, and transshipment) of a 40 ft container is much lower than twice the corresponding handling cost of two 20 ft containers. Enlightened by this observation, we propose a novel container routing with repacking problem in liner shipping, where two 20 ft containers can be repacked to a 40 ft container in order to reduce the handling cost. We develop a mixed-integer linear programming model that formulates the routing decisions and the repacking decisions in a holistic manner. An illustrative example is reported to demonstrate the applicability of the model. Results show that the benefit of repacking is the most significant when containers are transshipped several times.