Just returned from a 3 night trip to Key West. We scoured the Chowhound boards for ideas prior to leaving and wanted to report back.
Louie's Backyard (Upper Deck)--After a long day of travel we ended up here. Rather than the super expensive main restaurant, we visited the Upper Deck. Had a great view on the balcony looking out over the water. The menu is Tapas style and much more reasonable. Lots of wines by the glass. Our waiter had us try 3 to help us decide. And then left the bottle, indicating we would be charged for whatever we drank (of course, we drank the whole thing!). We had the cheese plate (with dried fruit and jellies paired for each type of cheese), pate and Ouzo shrimp. The shrimp was very fresh and unique. I was most impressed by the service and atmosphere--a view you can't beat!
Blue Heaven--Seemed very "Key West" to me. Started out at the bar and had a generous bloody Mary. The food is nothing outstanding, pretty bland, but the you go to hang out in the quirky environment with the chickens.
Seven Fish--OUTSTANDING! We made reservations to sit at the bar with Brent (per past chowhounders recs). It was raining and when we arrived all 4 bar seats were occupied. The restaurant is *very* small so we had to stand in the corner, in the way, for about 20 minutes. This was not handled well by management initially. We later learned that it is often a problem when it rains--people linger for a long time waiting for cabs. Brent DID comp us each a glass of wine at the end of the meal. The fish was excellent and fresh. Highly recommend that you get the fish of the day. The bar was comfortable, great service. Definitely need reservations
Camilles--Key West tradition. Great breakfast, big portions. Mimosas come with the rest of the champagne split :-)
Kelly's--We went *right* before happy hour, not realizing how important happy hour is in Key West. At 405 the place was PACKED! Great deals on microbrews--$2 for a pint, $4 wings (which were tasty). Arrive a little early to get a good seat.
915 Duval--Another outstanding dinner. Definitely sit outside so you can watch all the activity on Duval St. The service was impersonal and a little lacking. We really only saw our waiter when the food was delivered and at checktime. We split two small plates (plus cone of fries with aioli), one entree and cheese plate for dessert. Be sure to get "Devils on Horseback"--bacon covered dates. I could have eaten a whole order myself! For the entree we had the lobster and mussel dinner. Served like a cross between a stew and clambake. It was original, flavorful (if a bit messy). The cheese plate had a honecomb which was delicicious. Can recommend 915 without reservations.
We never made it to Siboney or Blackfin, unfortunately.