ROAD TRIP! It doesn't matter whether the economy is making you pick the car over the plane, or that you just really like driving through this wonderful country - everyone needs some time away from home, and taking the car is a fantastic way to see more than you can from 35,000 feet.I hadn't seen the Garmin Nuvi 855T before reading this and really like the looks of it's "Junction View". This shows you what road signs will look like where you need to turn. That would have saved me a couple of wrong turns on several trips.
I just took a road trip last weekend through five states (plus DC) and would add one more item to Gadling's list -- the Amazon Kindle 2. With it's text-to-speech feature, I was able to finish "reading" Tolkien's Return of the King on the trip -- alternating between actually reading it and listening to it. It made for a fantastic travel companion. What's also cool is that if you finish reading/listening to a book while you're still traveling, you can purchase and download your next one without worrying about finding an Internet connection.
My dad and I took a 30-day road trip across the country in 2005. Having GPS in particular would have made the trip much easier. (An MP3 player would have been nice too -- that was back in the days before I got my iPod.) Having said that, the important thing is to just get on the road. Technology may add marginal enjoyment/functionality to a road trip, but the biggest gain comes from just going. Gadgets might help make things more convenient and I certainly feel blessed to have the technology I have, but it is completely unnecessary to get out and have some fun.