You cannot travel to Key West without strolling Duvall Street. Stop in one or two of the more "famous" bars such as Sloppy Joe's or Hogs Breath, sit back and people-watch. I would patronize the "chain" places like Hard Rock or Fat Tuesday's only after experiencing the one-of-a-kind bars. The Duvall Crawl is a must-do, leave the kids at home for this one.
This is when you walk up Duval St from one end to the other trying to hit as many bars as you can! Take a taxi after or just walk (if you can!). Learned this from trolley car tour guide. Duval St. is the main drag where the shops and nightclubs are located. It’s a great place for window shopping, dining, and people watching.