What's the longest road trip I've ever been on? I'm not clicking on the main page link, since I don't do those, but my longest road trip was in the 70s. It was a family vacation. We drove from northern Arizona to Mexico City and back again - a three week trip, approximately 3000 miles roundtrip. We had 2-3 day stops in Mazatlan, Guadalajara, Morelia and a week in Mexico City. We went off-season, in July. People asked what was the hottest temperature we experienced during the trip: Coolidge, Arizona, at 118 degrees. Best weather: Guadalajara. Wonderful beaches: Mazatlan.
(I'm tagging this VW Bugs, but it doesn't really count. We *did* go in a Volkswagen, but it was a station wagen model.)