This could turn out to be a great thread!!
With the money, geography and dream car part out of the way......
I would take my wife. While she's a horrible navigator, we just bought a Garmin and that free her up to "help" in other ways...
Having seen WAY too many horror movies in my time I would have to take along some sort of firearm with LOTS of ammo.
Digital Camera with lots of MB's of memory.
Either a satellite radio or my iPod to help with the soundtrack.
All things being equal and I know this wasn't part of the question, but, I would have to make the trip in one of the new Year One Trans Ams...preferrably the higher horsepower one!
YouTube - the Burt Reynolds Edition Trans Am