I love Key West
When you get there, be sure to check out the Green Parrot Bar. It's at 601 Whitehead Street. One of my favorite places. They sometimes have "soundchecks" at 5:30PM usually Fridays and Sundays. It's a great chance to hear some really good bands. The soundchecks last for about an hour and a half and are a chance for that night's band to show off some of their best stuff. Usually soundchecks are packed, go early to get a good seat.