Going on a road trip with a toddler can be tolerable if several steps are taken to ensure the best possible outcome.
First, you must have your head examined. I would recommend a psychiatrist as well as a brain surgeon. The former will help evaluate your tolerance for sleep depravation, ability to overcome annoyances, ability to overcome mind-numbing screaming, and your sanity for considering this adventure. The brain surgeon will check to make sure that you do not have a tumor pressing some lobe that is causing you to feel that this is as good an idea as going to the local ice cream parlor.
I cleared both tests.
Next, have a good group. In addition to my wife and my son, we were also going to be with my brother and his girlfriend. We would rent a minivan and share driving responsibilities as well as the financial burden of $4.25 per gallon fuel prices. The plan included leaving at 8pm on Thursday night so that the child would sleep through as much of the trip as possible.
Schenectady, NY was the destination. The purpose: my aunt and uncle's 50th wedding anniaversary surprise party. According to Google Maps, the trip would be approximately 810 miles.
The only thing that did not go according to plan was my brother and his girlfriend joining us. This created a couple of problems. First, I would have to do all of the driving, as my wife did not pass the psychiatrist's evaluation. (11-14 hour workdays for the last 5 months will get a person teetering on the point of insanity and certainly at the brink of severe irritability.) Second, we would have to bear the $350 total fuel estimate. Finally, there would be nobody to entertain JD if he were to awaken.
The proper preparations for the trip were made. Car inspected and given the proper maintenance and cleaning. Snacks purchased. Plenty of caffeinated beverages. Bags packed. Coolers clean and ice available. Lots of diapers. Cash. Checkbook. Credit cards. I was on my game.