We drive at least once a year from Maryland, about 890 miles each way, door to door. (I guess we don't quite qualify for the 2K Mile club.
)
We're a family of five, but sometimes only two or three of us go, since two of our kids are now in college. Then we fly because we can usually get a $49 or $79 fare, we only do a 4-day trip, and it's worth it.
We live right off of I-95, so we hop on and head straight South. We generally leave around 10 PM and arrive about Noon the next day. DH does most of the driving, but I do about 3 hours around midnight, and now one of my kids can also drive for a few hours too. We have DVD players, play strange geography and trivia games, and always purchase one or two new CDs for the wee hours.
BTW, we get off I-4 at Sanford and take the Greenway East of Orlando. We've been doing this for at least five years. We'd rather pay $3 in tolls than drive even one mile of I-4 in Orlando.
Too many times we drove through snow and rain, keeping a good pace, and then the last 20 miles to WDW took two hours!
(Our family's greatest dream: Florida SunPASS could be incorporated into EZPass!)