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Motorcycle... That is much easier.
I would either start in New York and then go to DC, or start in DC and head for Nashville, TN. Going through the South, you will probably find more bikers. Then go to Oklahoma City, see the Midwest. Stop at The Big Texan resturant in Texas for the free 72oz steak, if you can eat it in an hour. Head for the desert southwest and the Grand Canyon. Make a small detour and visit Vegas. Head towards Los Angles. Then take the Pacific Coast highway to San Fran.
I think you could easily do some planning and do this trip for less than £6,000. Just being on your own schedule would be worth it to me. Gas, food and lodging shouldn't be that much. ~ £2,000. Renting a bike and insurance (auto & health insurance?) might be under £2,000. I'm not sure about getting a motorcycle license to prove you can ride, or if it can be transferred here. Then there are the airline tickets. It might be cheaper to get a round trip from the starting city to England, then get a one-way from the finish city to the start.
Bring a camera. It would be a great trip.
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