My wife and I just came back from Key West after visiting for the first time. While we enjoyed Blue Heaven, our favorite place was Kelly's, owned by actress Kelly McGillis. Pretty setting, good and reasonably priced food. We went twice in the 3 days we were there. We also recommend Croissentaries du France, where we sampled galettes-- cross between crepe and burrito. I would stay away from Conch Republic, overpriced and noisy.
ahh, Key West.. my sancutary. we're heading there in 2 weeks for our annual pilgrimage, this will be our 8th year in a row. Some of our favorite places include:
Blue Heaven for breakfast, lunch & dinner.. i have to profess, we don't go there for dinner as often as breakfast,(not anything negative, just creatures of habit and its our breakfast place almost every day we're there).. great juices, awesome banana bread ( you can buy some in the gift shop), great mimosas, awesome staff. There is one female bartender (I forget her name) that makes this awesome iced coffee with banana in it.. They have live music on Sundays during breakfast/brunch but NO MIMOSAS/ALCOHOL TIL NOON!! FYI..
Santiago's Bodgea 207 Petronia, for tapas is great.. I suggest the fresh yellowfin ceviche – marinated in spicy citrus juice and served chilled with fresh avocado, mango, and cilantro and the pinchos morunos spicy marinated skewers of pork tenderloin with apple-mango chutney.. thats my first stop when we arrive!!
Mangoes at 700 Duval.. its been fabulous in years past. I keep hearing things have changed, so we'll have to see this year.. their website is down too, so you can't check out any menus. We had a nice dinner out back under the trees and stars, you wouldn't know the back area existed from passing by on the street.
Antonias on Duval http://www.antoniaskeywest.com/ We've never had a bad meal.. i think we've had the same waiter every year too.. white table cloths but not pretentious. the homeade cookies at the end are a cute touch, especially if you have no room for dessert and want a little something sweet. THey double charged me one vacation and I didn't realize until checking my bank statement at home.. they quickly rectified the problem and sent me a gift certificate as an apology.
The Upper Crust for Pizza... what great pies they make!! I'm glad they're from Boston and i can get this at home!!
Square One (in Duval Square) http://www.squareonerestaurant.com/ Spectacular staff & service every time we've gone. High end American food. Nice outdoor seating. We went for breakfast once and I wasn't really impressed.. not bad, but will stick with lunch or dinner.
I just got back from Key West about a week ago.
Blue Heaven: We at there the first night we got into town because my partner and I had been dreaming about eating their yellowtail snapper since our last visit. Unfortunately, they were already out by the time we got there, so we were left ordering 2nd choices. I picked the Caribbean BBQ shrimp and my partner had the scallops. I was disappointed to find that some of my shrimp were rather rubbery. My partner's scallops were better, though. We ordered Banana Heaven for dessert(since we'd also been dreaming of that) and it was just as good as we'd remembered. However, had this been my first meal at Blue Heaven, I don't know that I would have gone back since there are many other good options on the island. The service was lackadaisical at best and our meals weren't anything spectacular. However, we decided we'd give it one more shot and go back another night to try for the snapper, and I am so glad we did. The meal was sensational. The service was spot-on - attentive and knowledgeable, yet relaxed. We were able to get the snapper and were not disappointed. Another person in our party got it, too, and was as wowed as we were the first time we had it. We finished off the meal with Banana Heaven again. Delicious. Like other people have said here and I experienced, it can be hit or miss. But when it hits? It's dang good. We've never had breakfast, but that's because we save our pennies for dinners.
Hogfish Bar & Grill: We ate there our 2nd night in town. We'd tried to find this place on Stock Island the first time we were down a few years ago, but were looking for it in the dark and missed the signs and ended up at the far inferior Rusty Anchor, which was very disappointing. Hogfish is not the most difficult place in the world to find, but it's not going to hit you right in the face. Anyway, I ordered the shrimp po boy, my partner had the fried hogfish sandwich(not The Killer version, though), and our friends had the lobster BLT and the Killer hogfish sandwich. I loved my po boy and the reviews were the same for everything else on the table. Our server was clearly busy with a bunch of tables, but she was great. The food came out quickly, super fresh and hot and the total cost of the meal was about $100 less than the previous night's meal at Blue Heaven. Different dining experiences, obviously
Salsa Loca: It's not the best Mexican/Tex Mex/whatever food I've ever had, but it was certainly solidly good and at a great price. I had the chicken chimichanga, which was actually two chimis, both stuffed full of flavorful shredded chicken. One friend had a pretty forgettable burrito, but our other friend loved her variety of enchiladas. My partner had shrimp fajitas that looked good - she didn't share! Once again, we had great service. I recommend sitting outside on the back deck.
BobaLu's Southern Cafe: We ate here with a friend who lives on Cudjoe Key. We'd actually eaten here on our last trip, too. We had fried grouper sandwiches this time - nothing fancy, just nicely done. Our friend says their other food is good, too. Again - it's not fancy and some things are probably hit or miss, but it is reasonably priced and is a good choice. Especially if you're starving after spending the day at Bahia Honda :)
Have fun! I didn't give you any undiscovered gems, but all of these places were solid choices(with the exception of Blue Heaven, but the risk is worth it, IMO).
If you search the boards, you're going to find plenty of Key West discussions, so I would start there if I were you.
But here are two, no three, restaurants I always return to:
Blue Heaven - I love them for dinner, but breakfast is my fave. Don't miss the banana bread.
Salsa Loco - Great little tex-mex place on Duval near Truman. My husband likes to return to Key West just for this restaurant.
Schooner Wharf - This is where I go when I want some simply prepared fish and I want to drink cheap beer with the locals. Very, very low key.
Others will suggest Sarabeth's and Louie's Backyard - both are excellent, but I tend to go to the more low key places when I "escape" to Key West.