My grandparents retired to Florida from upstate NY when I was a kid. They made the trip back and forth every Christmas and for the summer for 20 years (Grandpa was afraid to fly - plus it enabled them to have their car with them when they got here). Though I have flown plenty of times to visit them, when we decided to go to Disney we weighed the options and decided to drive. We left at night and drove non-stop, splitting the time between DH and I. We usually rented a mini van in Albany and it would take us about 20 hours or so from there. The cost of renting a van and gas didn't add up to the plane fares for four people traveling at Thanksgiving time (when we usually go) PLUS we had the added convenience of having a van while there, being able to pack food and a cooler to save on meal expenses, and not worrying about how we were going to cart or ship home our souveniers. It also enabled us to save money by staying off site some trips. The kids slept most of the ride and they really enjoyed seeing the different states - my youngest gets totally psyched seeing the "Pedro" signs as your approaching the border between NC and SC! Seeing all the states was also a fond memory of mine from my childhood trips. We also took advantage of being able to travel around Florida during our stay, spending a day on each coast and seeing the beaches and sites other than Disney.
When the kids were younger, I packed their handheld games and made them bags full of dollar store "to do" stuff like games, cards, puzzle books, disposable cameras, etc. We rented movies and brought the DVD player. I also made them activity books from printing stuff I collected on the net that were Disney related - coloring pages, puzzles, etc. In it, I added pages for journals for each day of their trip so they could write their thoughts and favorite things.
The one thing we had on our last trip this past November that we found the most valuable was the GPS. It made it effortless to navigate especially while we were in Florida.
Whatever you choose, be safe and have fun!