Ufda, lots of territory in a short time.
Ok, if this were me. I would blow off Jax and stay in an old inn in old town St. Augustine. That way you can explore at your leisure. Eat at Harry's for cajun, or cross the Lions Bridge and enjoy some of the finest shrimp on earth at a modest little cafe called Osteens. Hit A1A Aleworks for beer, it's right at the Lions Bridge on King ST at Avenida Menendez. There ia also an interesting art gallery a few doors down on King St. Take A1A outta there to SR 40. Very few lights, generally light traffic, and the road is right on the ocean. Lots of places to pull over and soak it all in. Not a bunch of ugly chain crap to ugly it up. Just a nice pleasant road. Someone else can fill ya in on the lower coast. Traffic will be insane, keep your head moving watching for 100mph Lambos and such. Floriduh City, lock and secure everything, just sayin'.
The top of the Keys is pretty much touristy stuff, but it has a charm. Lower Keys much nicer. Bahia Honda SP worth a look, and look for Key Deer on Big Pine Key.
Key West. Motorcycle parking is free in
designated spots. Do not cheat on the end spaces, I've been told. Hopefully you got a room right down in old town so parking/riding will not be an issue.
Be tolerant of homo/trans sexuals. Key West has the highest percentage of gays in the country, including Frisco. Do Mallory square at sunset, arrive early. Do not eat at the seafood buffet restaurant. Half Shell Raw Bar is decent, Paulie useta have a COG RTE there in January on an annual basis. There is also a cool tavern, I've heard, right to the right of it, same parking lot. We're heading down for a long weekend on the 22nd of this month, we'll be checking that tavern out. Otherwise just figure on wandering around like everyone else does. You may wanna consider Fort Zachary State Park, The Hemingway house, the light house,... We really enjoy it down there, some folks don't, some do. It's like leaving the country without going through customs.
A couple of highway notes. US 27 from Clermont(near Orlando) to Lake Placid now has about 57 traffic lights, and is snowbird hell. My ex SIL calls it purgatory, that name fits. It's pretty much all ugly, all crowded, with lots of slow semi trucks "racing" from said traffic lights. Avoid at all costs. The exact same thing can be said about US 19, pretty much from Clearwater to north of Hudson. It's all an ugly, congested nightmare.
When you come up US41, take SR 29 north to LaBelle, cut west on sr78 to sr31 north to sr70 in Arcadia, take a left. Continue through town, turn right on cr651. Continue north, it will change to cr653 after a while. Take it to sr62, then turn left, continueing to US301. Go north a little ways to cr683(Moccasin Wallow road), go left to I-75, take that south about a mile and take I-275 north. After you pay the toll, hit the rest are, very nice. Continue north on 275 to St Pete and work your way over to Fort Desoto Park. Then maybe Kegans Seafood in Indian Rocks Beach(Diners, dives, and Drive ins). After that, get the h*ll out of the Tampa/St Pete mess. No real good way to do that, maybe US19 north to sr60, east to the Veterans tollway, then head north. Central FLA north of Tampa area has some nice two lane back roads, with real corners and such. Very nice, uncrowded riding in the middle. Google up "sleepy hollow floral city" for an interesting place. Way cool, and nice folks that run it. And it's on a very crooked road in excellent condition. If you do go up on US19, just after Homasassa, take a left on cr494, take it to the end. An actual technical road in Florida. The Island Outpost, on your right as you are heading west, has pretty good Q from an on site smoker and alcohol free gas. Again, nice folks that run it. I think they also have live bait and ammo, what more could a guy ask for?
That's about it. Cedar Key is kinda cool, but seeing Key West first kinda wrecks that.
Other folks can fill ya in more, but that's pretty much what I would do.
I'll try to remember to do an update on that KW tavern.