In machining, the tool path is generated according to the workpiece geometry and arrangement of holes. Majority of Computer Aided Manufacturing (CAM) software offer a set of predefined strategies to choose from. These tool paths are mostly far from being the optimum path, specifically for complex geometries with non-flat surfaces. This thesis introduces a new algorithm based on Travelling Salesman Problem (TSP). The proposed local search algorithm generates an optimum collision free tool path in drilling operations. The developed optimization algorithm considers multiple constraints such as location of tool origin and presence of obstacles. Furthermore, a discussion on stopping criteria for the developed algorithm is presented. Obtained results confirm the proposed algorithm is capable of providing optimum collision free path with more than 50% reduction (in given examples) in path length compared to the HSMWorks software.