Thanks Bob.....I did some research and I find all the reviews are good. Tell me more about the "unique" characters....Im all about crazy people watching. Not much better when watching the sun set with a cold brew.

 

Catch the "circus" @ Mallory Square a couple of hours before sunset and toast the setting sun with the crowd. Check out the Half Shell Raw Bar for a cold brew and some decent grub. http://www.halfshellrawbar.com/ The Green Parrot Bar is another good stop.

 

Yo BB... I think it was sunset pier, can't remember but just ask anyone and they'll direct you. Everything from a guy painted completely white in a toga on top of a white trash can posing completely still like a Greek statue, a guy performing with a half dozen trained cats, pretty ladies, just about everything. Quite unique to say the least! Don't forget a picture next to the monument at the most southernly point in US.

 

It's Mallory Square. http://www.travelblog.org/Photos/5928962

 

*Seems like a lot of compressed seat time. Would the auto train cut down some seat time on the way down and arrive a bit more relaxed? The OVERNIGHT auto train takes you and your bike from Lorton Virginia to Sanford Florida(about 40 miles(1 hour) from Orlando or about 60 miles to Daytona/1.25 hour ). Might be able to avoid some questionable weather? and arrive in Sanford Florida area in the earlier part of morning and be able to get off and be in Daytona by 11am-12noon. This would give you about 3/4 of a day to see Daytona and then maybe another 1/4 day before a taking a ride to St Augustine (spanish fort & see the town ) the next afternoon (about 1 hour north of Daytona) with an overnight in St Augustine. Then leave St Augustine the next morning going south along the coast and see Cocoa Beach area and maybe continue to Ft Lauderdale Beach or further south to start of the Keys for overnight.
Daytona to Key West makes for a very long and time consuming ride(about 9 hours with-out stopping and enjoying the sites). Consider that from the start of the Keys to the end of the keys it takes about 3 hours + without stops since the speed is 35mph to 45mph and with plenty of tickets available(it is a slow slow ride) most people take 4+ to 5+ if they make stops to look/eat/drink.
*Again the Key West to Clearwater is a very long ride and would be more enjoyable avoiding interstates and traffic..again looking at another 8+ hour ride on interstates without stopping to eat or see stuff and riding full out the whole way. i will guess that you will NOT be taking the slower but more scenic (only taken during daylight hours) Tamiami Trail,SW 8, 41 across the everglades and then catching I-75 and instead will take alligator alley (I-75) if you are doing a straight shot...Might want to break that ride up if site seeing.
The full "free" day in key west is an excellent idea and a requirement. Consider finding a place with-in reasonable walking distance to Duval with-in your budget (nice to park once and relax especially if bar hopping) Parking sucks in Key West but there are plenty of Taxi although a short ride could be $10-$15..Panama City to New Orleans is about 7+ hours if you hug the coast in a few spots and enjoy a stop or two.>> Note that the Panama city SPRING RALLY is something like May 3rd to the 6th..
Google Earth is a neat tool that is FREE and is great in order to "see" satellite images of potential bike routes...10 days seems like a lot of time but is goes fast.

Here is a paste from one of my trips to key west:
If you like country type roads and it is daylight consider taking (997) krome south to the end were it will merge with (US1) at the very beginning of keys. **similar happens if you take the turnpike.. It will spit you out very close to the last chance saloon ”biker bar” and card sound road entrance.
Alabama Jack's, Card Sound Rd., On card sound road just before/right next to toll…Place to have a beer or snack. This is the only place to eat/drink on card sound road.
Key Largo : east side of road.. The African Queen ”bogart movie little boat ” - is on view at the Holiday Inn Key Largo Marina..”FREE” it is dry docked and the termites have done a number on it…can see it and leave with-out getting off bike…on west side of road: A local bar, the Caribbean Club-good view from the back and was supposedly used for Bogart movie…Get a beer in a bottle and enjoy view of water in back the leave.
Islamorada :Hand feed tarpons at Robbies(kinda cool)..really easy to miss...just past bridge..west side of road then under bridge.. I think it is $3 for bucket of fish and $1 dollar per person? nice 15-20 minute stop and they have cold glass bottle cokes to cool down.http://www.robbies.com/tarpon.htm

World Wide Sportsman, Islamorada - ultimate tackle store (now part of the Bass Pro Shop chain) but store has some fake history that includes Zane Grey and a Papa Hemingway boar replica(FREE). Good place to eat next door at isla morada fish company…Do not eat under roof “hot” eat at table near water….use bathrooms at the big world wide sports store next door..(back right corner) by the aquarium...(about $25 per person with 1 beer)
Seven Mile Bridge: used in several movies. Notice old bridge on west side...huge tree halfway down the ride.
key west
Mallory Square(FREE),Hemingway House $$$
Best fish sandwich : BO's fishwagon, fresh everyday, on caroline and William..dump at corner of intersection (about $20 for fish sandwich fries and a beer..park bikes a few feet away at meter..do internet search http://www.keywesttravelguide.com/bos-fish-wagon.html
Definitely get your picture taken at the Southernmost Point.

 

Nice....Im bookmarking this for my trip next spring. I wont be constrained by time Ill be stopping to see the sights. I may have to pick your brain when it gets closer to trip time.

 

that's it you guys haha! for some reason i thought it was a pier! it's been 17 years! (sorry) i think thats where trashcan man was too. nice pictures. i forgot that besides all of the craziness it's a cool and very pretty place. went to hemmingway house, lots of cats! if i remember correctly they'll tell you that some of them are decendants from hemmingway's cats.

 

And if you really want to see "unique" characters, go during Fantasy Fest. Adults only please.

 

Clearwater -- as others have said: Frenchy's for sure. Be there when the sun goes down. Good group of people. Great grouper sandwiches! You'll want to head up the coast from there to Tarpon Springs for a quick walk around -- feels like "Old Man & The Sea" setting.....

 

Capt Tony's is Key West is a good place for a beer.