As an essential application of unmanned aerial vehicle (UAV) systems, payload transportation has garnered significant attention in recent years. Collaborative payload transportation utilizing multiple UAVs can effectively increase the payload capacity of the transportation system. Nevertheless, the incorporation of multiple UAVs makes the dynamic model of the transportation system more complex due to the coupled UAV and payload states. In the immediate disaster relief response, the collaborative system is often required to promptly deliver supplies to the target site while avoiding obstacles to ensure the system’s safety. Consequently, devising fast delivery trajectories that avoid collisions for such complicated systems poses a considerable challenge. To this end, a novel trajectory planning method is presented for collaborative transportation systems. Specifically, the dynamic model of the collaborative transportation system is derived by utilizing the Euler–Lagrange method. Then, the trajectory planning problem is formulated as an optimization problem with considerations of dynamics, actuation, safety, and formation constraints. To expedite the optimization process, the collision avoidance safety constraint is constructed using dual variables. The efficacy of this trajectory planning approach is confirmed through multiple real-world flight experiments involving collaborative aerial transportation systems of two and three UAVs.