Came up with the idea of a webmaster road rally a few years ago. Something like the Gumball 3000
http://gumball3000.com/new/launch.htm
Spoke to some people in the biz, got good feedback. Had several sponsors lined up. Original plan was to start in SF, hit LA, Phx, and end up in Vegas at the Vegas Motor Speedway. In each location have a killer dinner and first class party.
With as many people in this biz who own great cars and love to show them off, there should be no shortage of participants. Of course a $100k car is not necessary. It is not a "race" ,as holding a race on public roads would not be legal.
Original plan was to have each party/dinner sponsored by a local company. Each car pay an entry fee, with a portion going to a charity. In theory, event would be for charity.
Unfortunately, I got caught up with other projects and never made it a reality. If someone wants to take the idea and run with it, I will turn over the idea and research we have done. As well as assist in any way I can.