You need a guide to follow the route, sights, history and be warned about the rough spots. Jerry McClanahan's EZ66 was mentioned, but I live by Tom Snyder's Route 66: Traveler's Guide and Roadside Companion and there's a recent 4th edition. It describes more of the actual route(s) while Jerry's offers more sights (thicker). The guides will tell you the location of the attractions and when you'll have to use your imagination.
We've driven 66 end to end except for the segment between Chandler OK to Tulsa and downtown Chicago. Probably 60% was with a crewcab P/U pulling a 29' TT or a 45' Super C. The 40% was with no TT or the toad behind the Super C.
We drove the Victorville to Barstow, Kingman to Seligman and Ludlow to near Needles thru Amboy recently in the Super C, but Topock to Kingman would be tough due to curves near Oatman. Barstow, Kingman and Seligman have museums or are just interesting. There's a Harvey House being restored in Barstow and Winslow. As was said, where there is a town along I40, RT66 went thru it. Williams, Flagstaff, Winslow (stand on the corner), Holbrook, Gallup and especially Albuquerque (Central Ave.) have tons of 66 scenery. The road thru the Petrified Forest NP is an old segment of 66. Much the same thru the rest of NM, TX until you get to OK City. There are excellent museums in Elk City, Clinton and El Reno OK. When you're out in the country, much of 66 from Seligman to Ok City is near or under I40, but landmarks have survived. East from OK City, 66 veers away from I40 and is close to I44, but pretty lonely to Tulsa. Not much is left from Springfield Mo to St. Louis.