Over the years, the design of the tip of available catheters and guidewires has evolved into various shapes whose geometry is mostly based on common sense and experimentation. However, while the tip shape of conventional instruments can be easily modified and tested, the length of the tip of a deflectable guidewire cannot. Hence, other approaches are necessary in order to determine the proper dimensions of original instruments. In this paper, we formulate the length of the different parts of the deflectable tip of a guidewire as an optimization problem with the objective to obtain a design that is suitable for cannulating several target bifurcations of the peripheral vasculature. A direct relationship between the design of the deflectable tip and the geometry of the target bifurcations was found and the optimal dimension of the tip of the instrument was computed. Following the length specifications defined by the optimization, a new prototype was assembled, and evaluated. The deflectable guidewire could successfully cannulate most of the pre-selected branches except those bifurcations with an angle α>70°. The latter limitation could be ascribed to the mechanical properties of the instrument.