I was really disappointed with my Key West vacation. Mainly because we're there during the record low temp days. None of the water sports activities were open, so nothing (literally) to do. The bars and restaurants were OK, very touristy. We eventually got to parasail (great!), but that's it.
I enjoyed the Hemingway house. I enjoyed the conch. And the drive down there. But other than that, nothing. I think we;re there just during the really bad week.
Hope you have a better time.