In the zigzag milling operation, an important issue is to design a machining strategy which minimizes the cutting time. An important variable for minimization of cutting time is the tool path length. The tool path is divided into cutting path and non-cutting path. Cutting path can be subdivided into tool path segment and step-over, and non-cutting path can be regarded as the tool retraction. We propose a new method to determine the cutting direction which minimizes the length of tool path in a convex or concave polygonal shape including islands. For the minimization of tool path length, we consider two factors such as step-over and tool retraction. Step-over is defined as the tool path length which is parallel to the boundary edges for machining area and the tool retraction is a non-cutting path for machining any remaining regions. In the determination of cutting direction, we propose a mathematical model and an algorithm which minimizes tool retraction length in complex shapes. With the proposed methods, we can generate a tool path for the minimization of cutting time in a convex or concave polygonal shapes including islands.