In modern product design, sculptured surfaces are commonly used for functional and artistic shape design. Design of sculptured surfaces is evolutionary, consisting primarily of incremental changes to existing part surfaces. Manual operation planning for sculptured surface machining is known to be error-prone and inefficient, which requires considerable checking, verification, and rework. Five-axis machining has higher productivity and better machining quality than 3-axis machining. However, the programming for 5-axis machining is more difficult due to the complex simultaneous cutter movements along the machine’s five axes. This paper presents a systematic methodology to generate operation plans for 5-axis sculptured surface machining. A complete operation plan and the error-free cutter path can be automatically generated from the CAD part design. To achieve design for manufacturing of sculptured surface products, the machining unfeasibility information can be fed back to the designer for further design modification. Results of computer implementation and testing examples are also presented.