Tad,
I hope I can help. I went to Islamorada two years ago hoping to catch my first bonefish. Here is what I found.
The good things.
1. The keys are a really cool place. Lots of things to see and do. My wife loved going 50 mph in the flats boat over the super shallow water.
2. We stayed at a place called Cheeca Lodge. Nice rooms, one of the better place to stay in Islamorada. Pretty good $$$ to stay there.
The bad Things.
1. Not a great place to go if it is your first flats type fishing trip. Islamorada has some of the largest bonefish in the world. They are also very spooky. Lots of pressure on them plus the weather elements (Wind!) can make fishing very difficult.
2. Guides - There are some old salty seadogs as guides in Florida. The first day I hoped in the boat, my guide asked if I had bought him lunch. At $425.00 a day, I don't think so. He should have bought me lunch and dinner. LOL
I fished two days with different guides and didn't catch any bones. I can't remember their names. We had shots, but like I said, not a great place to start bonefishing. Bonefish are spooky enough, permit are even tougher. I did catch some small barracuda's and got my first bonefish while fishing off the beach at Cheeca Lodge.
A buddy of mine who has fished Christmas Island bonefish several times fished there for a week without catching a bonefish. He went back this spring and got blanked on tarpon.
All in all I had a good time but was disappointed in the fishing. I know the keys offer some great fishing but it just didn't happen for me.
You may want to post this same message on Dan Blanton's Board. There are lots of people with flats fishing expierence there that my have other places / suggestions you my want to look at for you big 50 trip.
www.danblanton.com Good Luck,
Brian