Whether you do it on purpose (driving around town to induce a nap) or by accident (windows down, music blaring, begging baby to stay awake to no avail), sooner or later your baby will fall asleep in the car. Some people can get babies back to sleep after extracting them from the car seat, but that’s not the case with my kid. Sure, you’ll be delighted to see the blissed out look of baby sleep… but you might also wonder what the F*&k to do with yourself.
Here’s the tip: have a nap watching station all ready to go. With our house configuration, we can sit on the porch and keep an eye and ear on the car in the driveway. If you’re not so lucky, keep a lawn chair, cordless phone, and a stash of magazines (or your knitting), and a bottle of water handy. Instead of being frustrated, think of the blessed gift of time you’ve just been given!
Oh yeah, keep a close eye on the baby to make sure he’s safe and comfortably sleeping. 
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The times when I’ve gotten desperate and gone for the driving nap, I’ve either taken a book with me in the car (for once she’s asleep and I’ve parked somewhere) or taken my cell phone and the phone book to catch up on those annoying phone errands that seem to pile up. I’ll go through the drive-thru at Starbucks (before she falls asleep, they tend to wake her up with the speaker), get myself a snack, drive aimlessly, find a quiet, scenic place to park, and do my thing. In the spring and fall, there are a couple of parks where I can open the windows and park close enough to a bench that I can a) sit outside, and b) monitor her temperature to make sure she doesn’t get too hot while she’s napping. Mine was a hard-to-move baby too. It improved as she got older, though.
Another trick is to find places in town with free wifi, take your laptop or PDA, and sit in their parking lot (with latte, of course) for a while. Love that one. Didn’t do it often enough. (It also works if your house has a strong wireless signal, or if you have a neighbor who is lax with his network security!
At certain apartment buildings here in town, one can choose from 6 wireless signals at any given time. However, this may not be quite legal, so be careful to check local laws…)
I am an almost daily nap-driver. Rarely does my daughter transfer well out of the carseat once asleep. So, we have a system set up at home: a car outlet converter that allows us to plug in the base unit of the baby monitor to keep in the car with the little one and then we have the parent units with us. When it is nice outside we sit on the porch or deck while she snoozes. If it isn’t very nice, we can retreat indoors, all the while able to hear her breathe over the monitor. Luckily we have plenty of shade to park in so the sun doesn’t affect the interior temp of the car and when necessary we can leave the car running to ensure optimal temperature inside with the little one.
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