A few mates and I are thinking of doing Route 66 in the summer of 2009.
I found one place on the web that sorts out your flights, taxes etc, all the accomodation on the way down, as well as car hire for the 21 day duration (we opted for a longer trip, so we didn't feel we had to rush or cram it all in). I also added a few more days to check out San Fran etc after finishing in LA.
It was about £2000 (roughly $4000), which although pricey, still seems value for money. Especially since flights alone are so costly. And that also included hire of TWO cars, so should be cheaper as we only want one now.
We want to go in a Shelby Mustang (preferably the GT500). Again, I know this isn't the most comfortable motor to do the trek in, as well as being a bit of a 'guzzler', but it's what we want. Hertz do rent Shelbys, but cannot guarantee car model untill we arrive at the airport. You can imagine the dissappointment of landing in Chicage, to be told we haven't got one.
Basically, I've had a ganders on the web, but not much luck. If you guys know of any companies who rent/hire Shelby's and are happy to let us do the drive, that'd be really helpful.
In fact, any tips on arranging this whole trip would be welcomed, so too any tales experienced by those who've done it.
Thanks a lot.