Voyager 1
So far Voyager 1 has 'left the Solar System' by passing through the termination shock three times, the heliopause twice, and once each through the heliosheath, heliosphere, heliodrome, auroral discontinuity, Heaviside layer, trans-Neptunian panic zone, magnetogap, US Census Bureau Solar System statistical boundary, Kuiper gauntlet, Oort void, and crystal sphere holding the fixed stars.