If you are active duty, try staying at the BOQ, much cheaper then out on town.
Blue Heaven for dinner, fantastic food!!!!!
Duval st... favorite bars are Sloppy Joes and Lazy Gecko. Hog's Breath is at the end of the strip. Then you have the water front at sundown, that always draws a big crowd.
I don't know how to check, but if you can figure it out try and find out the cruise ship schedule. The streets get flooded with people when the ships pull in. If you can plan around it, I would.
Key West is awesome! Spent 3 great years stationed there at JIATF South.