A waterborne platooning concept, i.e. a Vessel Train (VT) it is composed of a fully manned lead vessel that takes over navigational responsibility for the followers. Joining a VT helps improve the competitiveness of smaller vessels and increase their use, as it allows a vessel to sail continuously with a small crew. This paper identifies the challenges created when penetrating urban areas and models the viability of the VT. The influence factors of the implementation hinge on the maximum opening times and on the simultaneous opening of adjacent bridges. The results provide guidelines for a successful integration of the semi-autonomous platooning system in urban areas.