Buy some of the Route 66 books that are available online. They describe where, when and how to get to the best areas.
You can still follow some of the old highway in Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona & California. A very scenic route is from Kingman Arizona west through the mountains down to the Colorado River.
Good Rt 66 books will give locations of long gone sites as well as some still in business. Lots of good recommendations for places to eat also.
Hope some of this helps. Being Florida puts you no where near the highway though.