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I will check with Mrs. TJ and get back to you. We had some fun there several years ago. I do remember getting some drinks and shrimp at this outdoor bar/deck type place where you can watch the sun set in the west into the Gulf -- quite cool.

Anyway, Mrs. TJ has a much better memory that I do and she'll probably remember restaurant names and the like.

My wife and I have been there 4-5 times. Here are some recommendations:

~Cafe des Artistes- Tropical French cuisine featuring local seafood. It has a WS Award.
~Cafe Sole- Franch Provencal cuisine.
~Louie's Backyard- A gourmet oceanfront restaurant. Nice setting.
~Michaels- A steak and seafood restaurant. I think there wine list is online at their website
~Eat it Raw Oyster Bar- No wine list that I remember. Very casual lunch place on the harbor.
~Dennis Pharmacy- A local breakfast hangout. Very unique and casual.

~Duval St.- There are any number of bars along this famous street including Sloppy Joe's, Hog's Breath and Jimmy Buffetts Margaritaville.
~Captain Tony's- I believe it is the oldest bar in the US. It is around the corner from Sloppy Joe's. Bring a business card to staple to the wall.
~Green Parrot- One of my favorite hangouts. Just off overcrowded Duval.

Things to do
~Rent a Scooter- It is the way to get around town. Can be rented by the hour, day or longer.
~Check out the sunset at Mallory Sqaure- Here is a sample.

Have fun.

I'm not there as frequently as I used to be since I became a Dad, but here's my take on a few of the recommendations so far:

Mangia Mangia - The only spot in the Keys where I have had a memorable wine experience. The Keys are designed to be laid back, so don't go expecting to be sniffing from a Riedel. I'm sure you can get Riedel somewhere down there if you try hard enough, but if you do you are kind of missing the whole point of the place to begin with. Therefore, Mangia Mangia is a laid back wine experience. The cellar (and maybe the restaurant) is owned by a wine lover, clear and simple. He's got a huge list at bargain basement prices. So low that he refuses to sell wines to-go. If you want to buy it, you have to drink it. Make sure you get a tour of the "cellar." It's a couple of rooms in a couple of houses, really wild. The food is basic Italian, the best seats are outside, but you're going in August.

Cafe de Artistes - I've eaten there twice, once with great success and once without. The one with success was over ten years ago.

Louis Backyard - Once the hallmark of Key's innovation, this venerable landmark has long lost its original luster, with the chef that gave the place its glitter long departed (try Norman's in Coral Gables) and service and quality back to Key West traditional standards, which isn't saying much.

So what to do? - As you might be able to tell from my comments so far, things don't stay the same for very long down in the Keys. Your basic hospitality staff isn't exactly thrilled to have to be working, they don't earn enough to afford to live there, and the simple fact that they are there hints at some sort of an unresolved inner turmoil to begin with. You can go to some of the national hotels that have bought property there and get a decent meal, but Key West without the "spice" isn't really Key West. And the "spice" doesn't do corporate.

Ask for local suggestions, and lots of them. If you can find a foodie or wino you’ll have it made. I’d suggest seeking out a place that will include the chef’s name “Alice,” maybe at LaTeDa’s but she might have moved, for some innovative cuisine. Don’t expect a lot from the wine list wherever she is, but her food should still be worth a bang for your buck.

BTW – BYO isn’t a problem down there. Also, August is VERY quiet, with the exception of a few German tourists (they are the really red ones). It’s the Keys, roll with it. [Cool]

It's late for me, I hope this post makes sense and/or helps. [Confused]
Forgot a few comments (told you it was late for me) -

Grand Vin - is a cool wine shop. You'll find things that are unusaul for the Keys, but not for the rest of the world. Whether or not you click with the local winos is something you'll have to figure out on your own. There's also a good wine bar across the street. (maybe I should say "was?")

In my notes I've only included places where good food is defined as more than the a good grilled or fried catch of the year fish sandwich (that would be dolphin, or mahi mahi to the confused), and where beer is not the beverage of choice.

Not that those are bad things in Key West, but I felt the need for the footnote nonetheless.
The best place to eat by far is a place called Seven Fish. It's at the corner of Caroline and Elizabeth St. The wine list is just ok but the seafood is the best I've had anywhere and I have eaten at a lot of seafood places. Go with the catch of the day or the recommendation of the waiter/waitress. The crab cake appetizer is to die for. I would recommend you get there when they open at 6:00 PM or make a reservation because it's a small place and by 6:30 PM people are waiting to get in. Decor is not much but I have not found a better dining experience in Key West. Entrees are about $20.00 which for the quality of food is a bargain for Key West standards.
Just got back. KW was very hot. However, I must thank you for the recommendation to go to Mangia Mangia. We went twice since we enjoyed it so much the first time. The menu is spare, but I had a great Tuscan Duck and the escargot was fantastic. Pastas are made fresh every day and delicious. But the wine, oh my, the wine list. It is quite long and extremely well priced. Unlike most places, the prices for older wines have not risen as they value has. I had a 93 Bongiovianni Borolo for $55 and a 94 Bernardus Barinus for $40. Exceptional prices for older first growths and at $275 the Gaja was very well priced. The list goes back to the 50s. French and CA wines are very well represented. The 97 Tapestry was $62 and the 96 $55.

Blue Heaven for breakfast was a joy. The Banana Cafe has wonderful food and great jazz on Thursday nights.

Mantus was good food and Mangos also, but both had wine prices that were out of line with the value, especially after Mangia Mangia's list. Had a great time and am planning to go back, maybe without the kid and not in August.

Had shrimp and grits for breakfast (Sunday bruch really) and a fish sandwich for lunch 5 days later. Both were out of this world. There was a young woman playing the guitar and singing at bruch. She was very good, I wish I had gotten her name. My wife had the jerk chicken and I must say it was quite good.

One other place we ate that I haven't mentioned was El Siboney at 900 Catherine St. Down home Cuban cooking. No wine to speak of (Sangria and table wine) but the food was good, cheap, and plentiful.

If you like ice cream, you have to go to Flamingo Crossing on Duval St. (1105) Best ice cream I have eaten in a long time. Wonderful passion fruit icecream, huge portions, and just the thing for a hot (and I mean HOT) day.

Marquesa one evening. Very pretty room, good service. Nice wine list, but a little pricy. They had a $27 three course meal that was a very good deal. I had the black grouper and enjoyed it very much. The grilled pork was a little dry however.

Camille's (spelling) was the place to go for breakfast when we didn't go to Blue Heaven. Huge omellets, good potatos, and great service. Very much a down home place.

Going in August was both good and bad. It was very hot, but not any hotter than here in DC. Since it is definitely off season, we were able to just walk into anyplace we wanted and be seated. They were so glad to have customers that the service was very good and not at all rushed or crowded.

Spent much too much money (gallerys you know)and ate too much (love those $4 a dozen oysters at happy hour at Eat It Raw)watched lots of sunsets and didn't spend a single minute on the beach.

We plan to go back, maybe this time without the kid, but not in August.
Coming late to this thread ("late" being the story of my life!)... but must second Jcocktosten's recommendation of Ambrosia as a great sushi place in Key West. In fact, of all the sushi places I've been to (from Tokyo's Tsukiji district to SF to NYC to Hawai'i to other Florida places), Ambrosia is one of my favorites.
Over the weekend trip to Key West, discovered that Blue Heaven and Seven Fish allow corkage. 6$ charge at Blue Heaven and $10 at Seven Fish. Offered taste at Blue Heaven and corkage was not waived. No complaint here, given it was a more than reasonable $6 and they brought us their nice stems without us even having to ask. Over all, very enjoyable. Corkage is more crucial at Seven Fish as their list is not very good, where Blue Heavan's is.

Missed you and your wife Emilio. Hopefully we can meet up down there some time soon. We are looking to maybe go back in October.
Board-O, it s a great place. Sports Jacket is totally unnecessary (as it is anywhere in Key West). I have worn shorts there (and to Cafe Marquesa, so you can anywhere). We have only sat at the bar for fondue, as the menu is a little meat heavy for us. However, the fondue is excellent.

I did not know about the corkage, thanks for the heads up.

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