Bayside Grill, Key Largo - MM 99.5 - lunch, on the bay, good views, my husband loved the fish sandwich, and I ordered a salad with grilled chicken, and found it lacking. I wish I had ordered the shrimp basket, it looked great. I think I just ordered the wrong thing, but the grilled chicken was very bland, and cold, meaning they had it pre-made, which I don't care for.
Morada Bay - Islamorada - MM 81.5 - dinner - The best! It was our anniversary dinner, and I couldn't have been happier with our choice of this restaurant. It is bayside, and has a beautiful beach to watch the sunset. We'd had drizzly weather all day, and the rain stopped just enough for the sun to peek behind the clouds as it set into the bay. The place has the atmosphere of an old beach house, and we had a table on the edge of the brick patio next to the beach. I think they put additional tables on the beach when weather permits, but not that night. They have Adirondack chairs on the beach, and I think it would be great to stop there for a sunset cocktail even if you weren't planning on having dinner there. The food was wonderful - We had the house salad (split), lamb chops, and seafood cioppino. The lamb chops were perfect! Add a good bottle of shiraz, a split desert, and we had a perfect dinner. They don't take reservations.
Zane Gray bar - next to Morada Bay, a clubby bar with live entertainment, in a very large sporting goods shop (World Wide sports?) We stopped in for an after dinner drink - nice place, but not authentic local stuff if that is what you are looking for.
Harriett's - Key Largo - Breakfast! MM 95 - Good, fast, inexpensive. Lots of locals eat there, and we had a very good breakfast. I first encountered my main issue with Keys eating here, though - few non-smoking areas. You can be seated, and the next thing you know, the guy next to you is lighting up - this happened in many of the restaurants we went to. I really hate that.
Calypso's - Key Largo - lunch - off the main drag - On the water (seaside), but that really doesn't add much to this place - I got the shrimp basket w/ fries, both of which where soggy. My husband didn't like their fish sandwich as well as the one he had at Bayside Grill.
Mangrove Mamma's - dinner - mm 19 -20. Very good food, service, fun atmosphere. Would definitely recommend it if you are in the area. They also had live music at happy hour (which we caught the end of). Carribbean-Keys style.
Fins 24 - MM 24 - lunch - very good, newer place. They have a nice outdoor patio in the back and good food. It was always busy when we drove by it at night, but we never stopped for dinner.
Blue Heaven - Key West - Great food, but don't let them seat you anywhere but downstairs in the back yard. We were seated upstairs, on the side porch, overlooking the back yard. We didn't notice at first, but after we were seated, we realized there were a few inherently bad things about the seating there - it was hot - the fence around the seating blocked the breezes, which led to more mosquitoes, and the noisy duct from the kitchen ventilation fan made conversation difficult. Add to that a smoker and a crying baby at the next table, and we couldn't wait to get out. No lingering over drinks or ordering desert, that's for sure. Not a good restaurant experience at all, even with a plate of good food.
The No Name Pub - after our KW experience, we escaped to Big Pine Key to find this local hang out. Lots of locals eating pizza and having beers. People decorate/sign/etc and hang dollar bills from every imaginable surface, interesting to look at. I guess I prefer the low-key places to the high traffic ones. You'll need directions to find it.