There's one crucial reason that Route 66 is a go-to choice for a retirement road trip: nostalgia. Stretching across eight states from Chicago to California, Route 66 is packed with towns that deliver neon nostalgia and kitschy Americana. There's even a train – the Grand Canyon Railway – that has been ferrying travelers from Williams to the South Rim since 1901. Aside from the Route 66 souvenir shops that line its streets, Williams hasn't changed much over the decades. On the way to the Grand Canyon, the nearly-forgotten Flintstones Bed Rock City is another kitschy pit stop.