I've gone to the Key West several times. We usually stay in Islamorada but drive down to Key West at least once.
In Key West you have to check out the Green Parrot!! Maybe my favorite bar ever. cool laid back atmosphere but a GREAT JUKEBOX!!! Check out the pic of the square grouper on the wall. haha
Hogs Breath is good, Sloppy Joes, Irish Kevin's, Captain Tony's, just to name a few. We hit 13 bars last time we did the crawl.
The Conch Bus tour is pretty cool cause you can get on & off at different locations allowing for the Duval Crawl, sightseeing etc. Hemmingway House is cool & there are 6 toed cats!!
If you have time go to Fort Jefferson!!! Very Cool & Historic.
Merlin Guest House is Ideal place to stay, close to Duvall & low key.
Have Fun!!