1972 Chevrolet K5 Blazer 4x4 4spd
Taking it's second appearance on this list, as I learned to drive a manual transmission in this truck (granny gear + gravel = perfect learning experience). I acquired it from my dad in May 2016 and drove it back to Texas from Colorado via a couple days spent exploring the plateaus and ranch country of New Mexico.
Mods: sweet canvas soft-top and a sweet Sanyo radio/cassette player (present when my dad purchased it). Currently no speakers though.
2016 - Current, but in the family since 1989.