In this study, we numerically investigated the nonlinear dynamic responses of an autonomous towing system where a vessel is passively towed by a tug via a towline. A three-degrees-of-freedom maneuvering mathematical model is utilized to describe the nonlinear dynamics of the towed vessel in calm sea. The hydrodynamic force acting on the towed vessel is modelled as a modular-type hull force model, which includes linear and nonlinear (third order) damping forces in sway and yawing directions. The towline force is simply modeled as a linear spring. First, the motion responses of a towing system, showing large sway-yaw coupled motions due to unstable towing characteristics, are studied by applying phase plane analysis. For the validation of the present numerical method, the simulation results are directly compared with the model test data. Then, simulation parameters, such as towing speed, initial positions and hull force coefficients, are changed and their resulting limit cycles are investigated. Finally, the effects of towline and tug motion are discussed based on the simulation results. It is found that the dynamic characteristics of the towed vessel come closer to being chaotic due to the nonlinear stiffness effect of the towline and tug motion effect.