Carpenter...rode there in 2009. Awsome ride. Miami sux and is huge. Theres north miami then miami then south miami, Stopped at Peterson HD for an oil change. Once past Miami it ws very scenic and breath taking as you crossed over the bridges.
We stayed at a Quality Inn if I remember correctly(under a 100$), right at the top of Key West just before looping around it. Was nice, clean and right next to a waffle house. I believe I saw a Ramada In but we pted for the Quality Inn because of its location and the convenience of he waffle house.
Theres much to see and do. There is Mel Fishers Museum (discovered the Attocha back in the 80's and is still bringing up gold). Then there is Soul pirate musuem, its sort of has a real cool Disney type technology to it.
https://www.piratesoul.com/Then there is MAllory Square and the awsome sun sets. Right when you think you've seen all of KEy West, you walk thru a gated type entry way and this whole nother section opens up. Mallory Square is cool.
A good place to know about is the concrete blocked building thats on street off from the main drag as you get into Key West, its for parking. Its 10$ but your individual bike is surrounded on both sides by concrete and there is an attendant keeping an eye on things.
And yes Sloppy Joes is a cool place to go. Good food and music. Ther is also a cloths optional bar...didn't go I imagine it would be a sausage fest. We went in April..wasn't crowded,temps were great and rices not so bad.
I'll post pictures later. Definately worth the ride and its a ride. BEware Key West is too full of whacka doos.