This disclosure is directed to systems and methods for providing a guiding device having a dilatable, drilling tip. The tip is formed by wound helical members such that resistance to rotation in an unwinding direction dilates the tip. The helical members are configured so that the dilatable tip increases in stiffness when the helical members are tensioned by a resistance to rotation in the winding direction. In some embodiments, application of relative force between coaxial inner and outer tubular members is used to control the dilation, stiffness and drilling of the guiding member.