A subintimal recanalization catheter, including an elongate shaft including a first tubular member and a penetration member slidably disposed in a lumen of the first tubular member. The penetration member includes a distal tip positioned proximal of a distal nose of the first tubular member. The distal nose of the first tubular member includes a ramp and a guide wire lumen extending through the distal nose of the first tubular member. Longitudinal movement of the penetration member relative to the first tubular member causes the penetration member to contact the ramp to direct the distal tip of the penetration member away from the first tubular member.