I have to get from San Diego to Tuscon, and I am considering driving instead of flying. I have never driven through that part of the US and it is featured heavily in a lot of car movies and magazine articles so I am kinda interested. Plus, the desert is very different from where I live and I kinda want to check it out.
Is this an enjoyable drive through a beautiful desert landscape, or 6 hours of sheer hellish boredom?
I've never driven to Tucson, but I've gone between San Diego and Phoenix a few times. It's not totally boring, but I wouldn't say there's 6 hours' worth of interesting scenery, either. :)
Double-check to make sure that your phone is set not to roam onto the Mexican providers before driving this route. It goes very close to the border, there are a couple spots where the US carrier signals are significantly weaker than the Mexican ones, and that can get expensive.
I drove from Vegas to San Bernardino once. Driving through the desert was pretty neat for a guy that lives in Wisconsin. I say do it.
Additionally, google says something like just under 6 hours to drive it. Consider the time it takes to fly and the costs. You'll probably come out ahead if you rent a car and drive it.
If you can avoid driving the 8 East for the drive it's pretty. My family and I just did a road trip to the Grand Canyon from SD. We went a little north to the 10 East so that we would pass through the Palm Desert and the original Route 66 (awesome BTW) in to Flagstaff.
The 8 is long, flat, and boring. Plus it's 2 lanes and can be frustratingly slow at times. It does go by the Imperial Sand Dunes though. If you have never seen them, it's probably worth it.
If you don't mind a longer route, drive up to Escondido, take 78 to the Salton Sea, then drop back to 8. Great mountain roads and much more interesting but add a couple of hours.
FWIW, any drive that takes <8 hours is worth saving the airport hassles to me. I drive all over the southwest. Sure, it can get repetitive, but there's a zen moment that comes through the boredom where you start to see interest and beauty in the sameness that is the desert.
Its not a bad drive, I do it a couple times a year. How long are you in town? If you want any input on places or whatnot just let myself or one of the other couple people from here know and ill be happy to help.
Plus if you drive we can show you some good driving roads here 
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