We do the drive from NY every year. We have a 2 year old son and 7 year old daughter. We have done the drive all different times and ways! What works best for us is leaving our house at 4am. The kiddies stay asleep and usually won't wake up till 8:30-9am. So we get a couple hours driving while they are still asleep. I bring breakfast with us and we stop for the bathroom in the morning after eating breakfast. We make sure when we leave to have a full tank of gas. We only need to fill it up about 3 times along the way. We bring drinks and snacks in the car so that means less stops for that stuff. We stop for lunch and dinner and for bathroom breaks and maybe 3 other times to let the kids stretch and run around with a ball at some of the rest stops. It takes us 18 hours door to door and we are about 90 mins from NYC.
We like leaving at 4am because we don't like to drive at night. We get too tired, we find the drivers are crazy at night and we just feel safer not driving then. Also I feel better going to rest stops during daylight! Some have security, some do not. We do like to drive straight through because we just want to get there!! We have no problem doing so. DH and I take turns driving.
To keep the kids busy we have tvs. One screen in each headrest and one on the dash for the passenger! We have a DVD player and the DVD's are easier to store, they take up less room than tapes. DD has her Gameboy Advance SP so she has games for that and they also sell the cartidges with nick toons and other cartoons on them. DH and I have our own IPods. I bring colored pencils, activity books, crayons, coloring books, word searches, stickers and such for DD. Also, travel magna doodle, travel colorforms for both kids.
The kids are really good in the car and are use to the drive. DD takes alot of naps, and keeps busy with all her activities, she's happy just drawing!!LOL We usually save the movies for after dinner, and we bring long movies, like Harry Potter. DS is mesmerized by the TV.LOL!!! Also, I wrap up little presents for them. Things I pick up from the dollar store. Usually I surprise them with one in every new state.
A tip that really works with keeping DD from driving us cazy is this: We give her about $10 in singles for her spending money for the drive down. To get something at the rest stops, like a special snack and such. Everytime she acts up or is bad we take $1 away from her. You wouldn't believe how behaved she is!!!LOL We do this in the parks too!!
We drive every year because DH won't fly. We have it down to a science and really look foward to our trips. It is good family time too. We often just talk to eachother and clown around and have lots of laughs. We try to make it fun.
Another tip would be to bring with you for the drive your own travel toilet paper and seat covers. Charmin makes them and they sell them at Target and some super markets. Not all rest stops have those paper seat covers, or even toilet paper some times! I have my own and they are small and compact and fit right in y bag.
Let us know if you have any more questions!