Hi Will,
As the person who started the Route 66 petition on here I'd like to thank you for including it.
I'm big fan of North America and have visited many Cities over there. Actually been twice with JY to Americas Golden West in 2010 and did Parks & Canyons earlier this year.
Now the holiday I'd most like to see is one that follows Route 61 (which bascally follows the Mississippi river).
The main cities on the route would be Chicago (my fav american city), St Louis, Memphis & New Orleans.
Other interesting places on route could include Vicksburg, Clarksdale (birthplace of the Blues), Baton Rouge, etc. sure there is more.
As you may have guessed I'm a fan of Blues Music.
But to be honest there is so many holidays I could think of that will suit many travellers, eg: American Civil War Cities, Northwest (been to Seattle which is good and Portland as a good reputation). Carolinas would be nice, etc.
I saw suggested somewhere two city breaks (say 5 nights each) with flights between for those that like cities and not long coach journeys, there is loads of options that cold be included.
Mick
Of course if you are struggling for tour managers I'm available, lol.