We went over 4th of July and I got some great tips from this board.
Duval Street is the main drag and it's basically a cleaner, caribbean Bourbon street. The nice thing is that you can get just one block or a half block off on a side street and it's totally different. Towards the north end it gets much more touristy with things like Senor Frogs, etc, as that is closer to the cruise ship terminals.
Danger Charters:
We did the all day cruise and they take you snorkeling and kayaking through Mangroves. We also did a sunset cruise that was fantastic. Only around 25-30 people, and the crew is super solicitous and fun. It was a "wind and wine" tour and they take you through like 8 bottles of wine to taste. Can't recommend this outfit enough. They'll let you do as much or as little sailing as you want, let you swim, show you all kinds of fun wildlife. Just fantastic.
Breakfast:
Banana Caf amazing crepes and brunch
Ana's Cuban Caf this was my favorite. A window counter in a old house, and people just walk up and order and eat on the porch or get it to go. This was seriously amazing
Camile's more of a local place, and the waiter tipped us off to some great spots for happy hour
2 Cents we went here for happy hour and for brunch on Sunday. Phenomenal gastropub with great drinks and drink specials. Seriously amazing. My favorite place
I think we did Nine One Five one night (or the place upstairs from it) and it was good.
Flaming Buoy was probably the best meal of the week fantastic food. The restaurant was back in a neighborhood, and it was kind of hot but the food was amazing.
The big thing at Key west is sunset happy hours. They'll tell you there aren't really beaches there and they are right. Don't expect Destin like beaches. Get out on the water and you'll have a blast. They have great jet ski tours too.