Thanks to posts from this board, I had some pretty good dining experiences on my short visit to the Florida Keys. Here are the highlights (and one lowlight):
Wahoo's Pub and Grill at Whale Harbor, Islamorada (on Highway 1)
The Wahoo's Raw Bar is a great deal for $14.95 that includes oysters, mussels (sometimes), shrimp, crab legs, and a chilled seaweed salad. It's on the appetizer menu, but it's enough for one person for an entree or two people if you buy a second appetizer. The beer is good, but stay away from the mixed drinks--they seem watered down. The mojito tastes like ginger ale. Maria, my server, was the best! She's a great local character and a fantastic way to start the trip. Ended up returning on the way back to Miami and Maria was stellar once again.
Blue Heaven, Key West
Previous posters were absolutely dead on with this place--it's fantastic. I got excellent service from Sean who did a great job dealing with a couple minor problems and helping with questions. I had the Rooster Special with eggs, grits, pecan pancakes and the spicy sausage, and it was a terrific deal at $7.95. Held me over for a busy day, and there are some really handsome chickens and roosters roaming around while you eat!
Turtle Kraal, Key West
Recommended by a bartender and a cab driver. It's next to Half Shell, which was what I was actually looking for, based on recommendations from previous posters. Really good conch ceviche and lots of local color.
Key Lime store in Key Largo on the east side of the highway--can't think of the actual name of the place
Great key lime pie--I don't like a whole bunch of fluff on my pie--this was basic key lime custard without food coloring with a little bit of whipped cream. Perfectly tart and not too heavy.
The lowlight? Drink stand right by Mallory Square--can't remember the specific name of the place--it's bright yellow and right on the Square.
If you're ordering a drink expecting that there's actual alcohol in it, you'll be disappointed. After paying $10 for a drink, I discovered that they use "wine based" liquor (which doesn't make much sense) and it's 10 proof. Skip the drink at Mallory and go someplace else.
All in all, a great trip. Will need to go back someday soon!