I try and reflect wherever the road trip is. For example, my circa 20 hr oad trip in Florida this Fall (already getting into it) will include the Scarface soundtrack (simply amazeballz) and Vanilla Ice's epic 1990 debut album, To The Extreme (he was raised in Florida). I may also try and get the theme tunes from Gentle Ben and Flipper. Tom Petty and The Drums may well feature, there's a strong chance there'll be one track by KC And The Sunshine Band too.
However, there will be no Backstreet Boys or N-Sync despite their Floridian roots. I'm not certain Gloria Estefan is going to make the cut either.