>>3113082This.
Especially the part about renting a bike for Key West the whole island is 12 square miles when I used to do the Keys monthly I would bring bikes down. Hang a left at the light and follow the seawall there's free parking and you can ride a bike from there to anywhere in the island in 15min.
Also hit The Cafe, off Fletcher St. You also have to do Mile 0, which is near the courthouse on Duval. Also do the lighthouse, pic related. There's a burlesque house that does a drag race periodically on Duval St. and not the kind with big-block Chevys.
If you can time your arrival into South Florida at the end of the month, the last Friday of every month is Critical Mass it is a giant ass bike ride through downtown Miami with literally thousands of bikes and sometimes the Miami Heat players show up, I got to meet Lebron James when he played for them, dude has hands like a fucking silverback gorilla.