[Jim in CT]

My favorite place on the planet, I have been 9 times.

Head to "Mallory Square" for the daily sunset party. On the west side of the island, street vendors and performers (jugglers, sword swallowers, dog trainers, etc) put on a show for the folks there to watch the sunset. It's a fun place to hang out.

Food - get a blackened grouper sandwich and conch fritters at B.O.s fish wagon. Awesome lunch.

If you go fishing and happen to catch snapper or grouper, bring it to the Hogfish Bar And Grill (technically on Stock Island, which is just a couple of miles north of downtown Key West). We did that last May (brought our fresh catch for them to cook up) - BEST SEAFOOD OF MY LIFE. My wife and I were absolutely blown away. Great casual pub, located adjacent to a marina.

As posted previously - go to Blue Heaven for breakfast, and if you don't mind spending $35 per person for breakfast, get the lobster eggs benedict. Unfreakinbelievable.

I also had an awesome Cuban meal at a place on Key West called El Siboney. Pork, rice, fried plantains, MAN it was good. And this is not a tourist joint, it's where the locals go...

I believe one of the waterfront restaurants along the wharf on the south side (it's a small area) used to do daily tarpon feedings in the afternoons. That was neat to watch.

One of my favorite bars there is a place on Duval called Irish Kevin's. A couple of nights each week, they have a guitar player who combines acoustic guitar with profane comedy. I have seen him a few times over the years, he puts on a decent show.

Park in one of the large municipal lots near the south side, walk along the wharf, lots of cool, casual bars and restaurants.

Have fun. Leave your watch at home, you won't need it! And post a report, let us know what you liked and what you didn't like...man I'm friggin jealous, I'm not sure when I'll get back down there again, I just know it won't be soon enough...I got a bad case of Keys Disease, I believe I am the Index Patient...