I had 3 rules on the first trip. 1. no interstate. 2. No fast food. 3. There's no rules.
on the 2008 trip, we road straight to Mexico Beach(pre-hurricane wipeout) and took a left. I stayed as close to the coast as possible. Every time I could see the gulf, we stopped to take in the fresh air. Being from the north part of the state, we get excited over fresh seafood. We stopped at every local place we suspected seafood was served. I know that won't mean much to you. lol
Sanibel and Captiva Islands are nice stopping points. Everything is pricey on the islands. The Mucky Duck on Captiva offers a great sunset view.
Nice ride across Fla to get to The Keys. First night ate at Lazydays on Islamorada. Get there early or make a reservation.
We just walked around Key West for the day and ate at Sloppy Joes, good food. Also took the Southern Most Buoy pic.
We traveled north on Hwy 1 along the Atlantic Coast to Daytona and Bruce Rothmeyer HD, world's largest Harley dealer. Worth the stop even if you don't have a Harley.
On the 2016 trip, it was a hair on fire Iron Buttesqe ride going down. 800+ miles in 15 hours. PSA -- Don't have battery issues or fall over before you make the first mile.
You can wheelie through an intersection while the local popo looks on in the some Ga. towns.
Take the trolley ride around Key West. Then go to Mallory Square to watch the sunset and the street performers is a must. Get there early.
While at Mallory Square, be careful with who you are around. Strange happenings have been reported.

When you get to Goodtimes Motel and Marina, tell Martin and Dawn that Johnny and Sandy says "Hi".
Enjoy your trip.