When I was very young (0-7), my family did road trips with a smallish station wagon. Was my mom, dad, me and my baby sister. We went to Orlando, Minnesota, and various places in Wisconsin and Michigan. Don't remember that much of it.
In 1987 my folks bought a van (full size Chevy van.) And we had tons of space. The van was great for road trips with mom dad, sister, brother, me, dog, and all sorts of camping shit or just luggage, or if we brought uncles / aunt/ grandma / cousins, etc with us. It wasn't a conversion van, it was just a full size van with 2 seats in front and then 2 benches behind and then another 6 or so feet behind the second bench for "stuff."
Anyhow, it was a good road trip car, though the fuel economy was horribad.
Since then I have done a few road trips in my 1994 Grand Am (2000ish went to South Dakota, 2002ish New Orleans, and many times Wisconsin.)
I've gone on some road trips with my 1999 Chrysler 300m (South Dakota to visit family acouple of times 2003ish, 2006ish, and several trips to wisconsin, michigan, quad cities. Trip to St Louis in 2007 or 2008.
In my current car, (2008 forester), I've gone to New Orleans, Baltimore, South Carolina, and various parts of WI and Mi over the last 3 and half years.
I generally like road trips of 300 miles or less the best, anything more than 5 or so hours starts to get uncomfortable.. But, I'm willing to drive 1000 miles every once in a while... Had great fun the last time I drove to New Orleans, had awesome fun in South Carolina, and I enjoyed my last cruise which departed from port of Baltimore.
Fiance and I are both working on losing some weight, and hopefully when we are a bit less enormous, maybe she'll be willing to fly, but until then, I'll drive wherever we go.