Key West in Nov.
The key to good food in Key West is to stay away from the tourist traps. For the most part, everything you find on Duval Street itself is going to be tourist-y.
5 Brothers is good... and a spot for locals. There is another really cool convienence store (I recall calling it "Seven Days") on a corner inland... adjacent to the elementary school. They had the absolute best steak sandwich I have ever had in my life- I have been searching for something similar for the past 15 years. I can't imagine that they would move... if you can find a current local, you might ask... it is so worth it.
I hear that Kelly's makes a marvelous mojito (a favorite of mine). http://www.kellyskeywest.com/
I would strongly suggest a cup of Baby's coffee (if you are coffee people)... it is a local coffee that can't be found elsewhere. http://www.babyscoffee.com/ Last I checked, they had a store on the easternmost side of Duval.
There is also a phenomenal pastry shop (in the morning) that is just west of US1 on Duval... it can't be missed, as it usually has lines of people.
The other "must" for me whenever I go down, is a trip to Flamingo Ice Cream. Again, this is on the easternmost side of Duval (really, I think, a few steps away from Baby's). This is homemade ice cream in the most deeeeelicious flavors. A perfect treat for strolling.
I'm not sure where you are coming from, so I don't know if you are familiar with cuban or caribbean cuisine... Those flavors and tastes are probably the most authentic to Key West. Conch fritters, fresh dolphin (there are many local fisheries, so almost every place can get fresh fish), fresh fruits...
A lot of people go to Margaritaville, but it is a colassal waste of space as far as I am concerned.
Also... again, I dunno where you are coming from, but there is a sandal shop in Key West- called Kinos. It is a Cuban family owned and run factory- the sandals are the highest quality I have every seen. I have worn some of my pairs daily, for the past 15 years- and they still look great. It is the high quality craftmanship. Moreover, they are CHEAP. Like $7 a pair. $7 for sandals that last 15+ years- THATs WHAT IM TALKING ABOUT! Kinos. They are near Mallory Square, one block south, across from the cigar shop. (I know this has nothing to do with food, but those Kinos are incredible). :) :) :)
We do weekend trips to KW 4-5 times a year and Santiago's is always one of our stops.
I was disappointed in Blue Heaven after reading up on it. Very pedestrian.
Hot Tin Roof was very good, but the chef has changed since we last ate there so I don't know how it is now.
7 Fish was very, very good. The warm grouper roll was one of the more memorable appetizers I've had in a long time.
We live down here and I agree with most of the previous posts, especially Bayou Teche. Except for Louie's, friends who have been there recently were disappointed.
Michael's is great for steaks and are well known for them, but I always get fish there and am never disappointed. They also have a special bar menu, if you ever just want a drink and something light.
7 Fish is my favorite place for Fish in Key West.
Pepe's on Caroline St., for breakfast.
Meteor Smokehouse is a great place for lunch or late night dinning, as they serve the same menu until 3:00 a.m. They have great pulled pork and brisket sandwiches, try the spicy green beans, and my favorite is the house salad with grilled fish (usually Mahi Mahi, blackened or not) on top.
If you are driving down, or have a car and want another great choice, head up to MM24, Cudjoe Key, and eat at the Square Grouper. It serves lunch and dinner. (closed Sunday & Monday)
In Sugarloaf Key, MM18 , Kingston's Clam Bar, is also very good.
My son and his friends like to stop at Mr. Z's, just off Duval, on Southard, for sandwiches and pizza.
7Fish is excellent, all the way around. Be sure to make a reservation if you plan on going because the place is tiny and fills up fast.
Santiago's Bodega was good, but they hadn't cleaned the cloth covering the benches in a very long time and it distracted us considerably from the food. It was the middle of the day, and very bright inside, so we could see every little food stain.
El Siboney, like others have said, is wonderful.
Turtle Krall's was great for breakfast. I'm sure it's just as good other parts of the day, but b-fast was comforting and plentiful.
Sarabeth's was very good. If you're craving fried chicken, hit up Sarabeth's on Sunday night. It's excellent. We didn't make it there for breakfast, but that menu looks good, as well.
Blue Heaven is a tourist turn-and-burn, but we liked the bartenders, the setting, and the roosters. Food was only slightly above average, but it was fun.
Kelly's also has a great setting and they brew their own beer. Didn't eat there, but the beers were good and it had a great atmosphere.
Our fav was El Siboney, grilled chops and vaca frita were yummy, generous, and affordable. I liked the cuban mix sandwhich at Sandy's better than 5 Brothers personally. The Good Life had great grilled cheese and tomato soup appetizer. For dessert our best was banana bread bananas foster at Blue Heaven. Loved the savory crepe at the Crepe stand on Duval. Croissants de France had a fabulous grilled brie sandwich on brioche-add bacon and it's the best sandwich ever! Camille's had a wonderful omelet but I found their french toast over-rated.
We tried Tavern 'N Town on our last trip (end of Oct.) and found it to be very good. It used to be affiliated with Norman Van Aken, but I don't know that it is anymore. The fish was very fresh and came out piping hot. I also enjoyed the pomegranite mojito. The Havana Banana Split is almost identical to the banana dessert that was served at Norman's in Miami for many years. Yummy. The restaurant is located in a new hotel that is just off the highway on the right almost as soon as you drive onto the island. Sorry I can't recall the name!
Town and Tavern is in the Beachside Resort. It is very good also, they have a great "Happy Hour" there, with 1/2 price appetizers.
Ambrosia is also a good choice for lunch or dinner. It's located in the Santa Maria condo/hotel. They offer very good Japanese and Sushi. At lunch they have a "Bento box special" which is great. The sushi is top notch, and reasonable.
We go to Key West quite a bit. We no longer go to Blue Heaven although, I do like their banana bread, because I always feel like I am fighting off flies something that does not happen in any other place where we eat outside. We love Michael's, we go there every trip. Louie's is very uppity IMO. Probably will never go back. A member of our party asked for a drink with a flavored vodka and was told the owner doesn't like flavored vodkas so they don't have them at the bar. Too bad for what the customer who is spending big bucks there likes or wants. We love Sarabeth's for breakfast. I believe they are not open on Monday's.
Thanks for all of the suggestions. We just got back from a wonderful trip. Here's our rundown:
We were a bit hampered because hubby uses a walker and has a service dog. The scooter arrived 2 1/2 hours late(not a big deal) however, it was enormous and would not be practical at all for him to use. I should have specified that it was a mobility scooter. 4 Stars rental said we would still have to pay a 4 hour minimum and the drop off fee ($120). In the meantime, I arranged to rent one of the 4 seat electric cars at a dear price for 5 days of the 7. It was that or stay at the hotel for the entire time. The hotel concierge arranged for 4 Star to cut our cost in half and the hotel picked up the other half! The hotel, Hyatt was wonderful!
Places we ate:
Damn Good Food To Go- for take out breakfast. OK for a quick takeout breakfast. Staff was wonderful.
Shor Restaurant at the Hyatt- Great crab corn chowder again, very friendly staff.
Rum Barrel- good Philly Cheese steak "wit'. Had salsds the next day that were good, but nothing really special. Bartenders were very personable. if you are an Eagles or Phillies fan, this is a good place to meet people with like interests.
Cafe Marquesa- wonderful dinner. The rack of Lamb was really yummy. Hard not to pick up the bones and gnaw on them.
Southernmost Beach Cafe-interesting twist on calamari, with pepperocini rings. enjoyed the "horny parrot" (Malibu rum, peach schnapps, pineapple and cranberry). The location was perfrect and out of the windy north part of the island.
Sarabeths for a wonderful breakfast. The french toast with almonds and cinnamon was really yummy.
Margaritaville-bar food. Had to go for the experience...
The Thai reastaurant- did carry out. not horrible but a bit disappointing.
Places we drank:
all of the above except the breakfast stops
Louie's Backyard-personable bartender. View was perfect.
Hogsbreath=nice entertainment, watery drinks
Island Dogs Cafe- a neat place to watch everyone walk by. Did carry out of burgers that were ok, nothing special.
We hit a lot of the standbys, but it was my first time there. Would love to have gone to the Cuban place, but ran out of time. Already planing the next trip...
This is a dream post and string of replies! Thank you to everyone that contributed. My parents and I are taking our first family vacation to Key West in over a decade and this post allowed me to create a wonderful list for breakfast, lunch & dinner or whatever craving strikes us.