I put on 4-6k (10k one year) miles a year traveling between Denver and Chicago to visit family and what not. So here are my 2 cents. Maximize daylight driving hours. Driving straight through the night used to sound appealing when I first started making those 1000 mile road trips but I soon realized they are a LOT harder on you and sleepiness is always a factor regardless of how much coffee or energy drinks you consume. I used to work 3rd shift and thought I was used to staying up all night but the pre-dawn hours seem to be the worst even for a seasoned veteran. As far as listening materials go, I always load up the iPod with with audio books and podcasts. By hour 5 or 6 listening to the same songs you have heard thousands of times on your iPod will get pretty boring and having a human voice to listen to will keep you more focussed while you drive. Staying properly hydrated is critical so I bring plenty of water and other beverages. Lately, I have cut out coffee and energy drinks completely. I find that they make me feel "not-so-good" when combined with hours upon hour of driving. Other than that, I buy a pack of cigarettes. I almost never smoke cigarettes otherwise but I feel that they make the road trip a little more bearable for some reason. Probably not the healthiest option though. ....and that's how I do it.