Route 66 -- United States
The route: We're not about to leave this tarmac testament to 20th Century America's wanderlust off the list. The 2,400mi "Main Street of America" crosses eight states (from Illinois to California) in a salute to all things Americana, from open road and kitschy tourist shops, to retro gas stations and diners packed with vinyl booths -- plus three of the country's surviving wigwam motels.
Pit stop: What better way to commemorate your country's heritage than with a 72oz slab of heart-attack-inducing red meat? Stop by Route 66 institution the Big Texan Steak Ranch in Amarillo, TX, and tuck into one of the country's most famous eat-it-or-buy-it binge contests. Too full to finish? Be warned your glutinous gamble will set you back $54.13, tax included.