In computerized tool path programming, the operator/user can generate the tool path based on the shape and geometry of the part to be produced by choosing from a set of predefined strategies available in the library of Computer Aided Manufacturing (CAM) software. These tool paths are typically not optimum, specifically for complex geometries. This paper employed Travelling Salesman Problem (TSP) as a foundation to propose a new tool path optimization algorithm for drilling to minimize the tool path length and subsequently reduce the time spent on nonproductive movements. The proposed algorithm was solved using local search approach in the presence of multiple constraints including geometric obstacles and initial location of tool origin. The outcome was a near-optimum tool path for drilling operations with no collision with workpiece features. The computational efficiency of the proposed algorithm was also compared with other methods in available literature using a standard workpiece as a benchmark. The results confirmed that for given examples, the near-optimum collision-free tool paths using the developed model in this paper were almost 50% shorter than the tool path generated by a commercial CAM software.