We went to Key West a few years ago (just one day on a cruise) and enjoyed the Trolley Tour there (http://www.trustedtours.com/store/Old-Town-Trolley-Key-West-C220.aspx) - it is a good way to get an overview of the area and a feeling for the history. I also quite enjoyed touring Ernest Hemingway's house (http://www.hemingwayhome.com/) - it is a stop on the Trolley Tour and is interesting to see a example of a house from that era.
Hi,
We like the Hogs Breath bar. The food and beer's good and they have a streaming webcam so you can say hi to the folks back home and make them jealous at the fun your having.
Hi Steve and Sarah,
I agree with Boo - In Key West, definitely do the Trolley Tour! Visit Mallory Square for all the street entertainers, and have a Sloppy Joe in Sloppy Joes on Duval Street!