A catheter system and method of dilating first and second anatomies includes a guide catheter extending along a longitudinal axis that has a breakaway distal end portion with a conduit in communication with the lumen. The conduit is configured to guide a dilation catheter at a first predetermined angle relative to the longitudinal axis and a second predetermined angle relative to the longitudinal axis for respectively dilating the first and second anatomies. The breakaway distal end portion includes first and second guide segments at least partially defining the conduit and respectively extending the first and predetermined angles to first and second distal openings. The second guide segment is removably connected to the first guide segment for selectively guiding the dilation catheter along the second predetermined angle when connected and along the first predetermined angle when disconnected.