This study aims to improve the efficiency of free-form surface machining using a five-axis controlled machine tool and a barrel tool. The barrel tool has cutting edges, with curvatures smaller than the radius, thereby increasing the pick feed width compared with a conventional ball end mill with the same tool radius. Hence, the machining efficiency can be improved. To use barrel tools effectively, it is necessary that they be utilized in a five-axis controlled machine tool. In the case of five-axis controlled machining, tool interference may occur, which should be avoided during actual machine operation. Moreover, a sudden change in tool posture adversely affects the quality of the machined surface. In this study, a method to obtain the cutting points that render the cusp heights below a target value is proposed. Moreover, a method of generating the interference-free tool path, in which the tool posture changes continuously, is proposed. The usefulness of the developed method was confirmed through machining simulations.