J and I had a wonderful time eating our way through the keys. As with any trip, there were some highlights and some low points but we did find that we loved the bountiful and incredibly fresh seafood and our favorite restaurants were Herbies in Marathon and the Shrimp Shack on Stock Island. I was disappointed with El Siboney (Key West) though they had great reviews on Chowhound, etc and didn't really like the food at Tony's (Key West). Here are a few photos from our trip:
On our first day in Key West, we had lunch at Tony's Cuban cafe. I ordered the Tony's special sandwich (grilled sandwich with ham croquettas and pork) and J ordered the Cuban sandwich. I thought my sandwich (bellow) was a bit greasy and the croquettas did not taste homemade. I was disappointed to get such poor quality so close to Cuba!
This is a pic of the house sandwich (Tonys sandwich) with the suspiciously prepackaged looking croquettas.
For dinner that night, we went to lobster fest (going on the day we arrived in Key west) and had some grilled Caribbean lobster. This was a bit pricey at $32 for 2 lobsters but still very good! My recommendation, go to Stock Island and order at whole lobster at the Shrimp Shack for $13 instead!
We had key lime pie at the Blonde Giraffe in Key West. I found this pie to be a bit gritty and did not like the meringue which tasted like it had been sitting around for too long :-( think this is a case of quality going down after winning an award (see Woodchicks post for a similar dilemma.)
The philly cheese steak at Guy Harvey's Island Grill in Key West was actually really good (we were surprised!) Apparently, he flies the bread in from Philly, they also have $1 drafts, can't beat that deal!
J sitting at the Shrimp shack on stock island. The food here was amazing! Definately go if you get a chance, only 10 minutes or so outside of Key West. 
Grouper sandwich with homemade tarter, incredibly fresh, moist and delicious! Jason ordered the shrimp poorboy and we split a grilled lobster. This restaurant is inside a fish market and the food is wonderful! Notice the tarpon finning in the background.
These are pics from our favorite place in Marathon (and the Keys for that matter), Herbies. Above are photos of the scallop cakes and the smoked fish dip (Yellowtail, I believe.) The fish dip is smokey and creamy served cold with crackers and the scallop cakes have some filler (bread or cracker crumbs) with generous amounts of chopped sea scallops that were amazingly fresh. I have never had a scallop cake but loved the idea and plan to try to make these at home. These were so good that we ordered them both times we visited the restaurant.
closeup of the amazing smoked fish dip at Herbies mmmmmmmm
Herbie's wonderful scallop cakes close up (sorry about the glare from the dish)
Jason ordered the stuffed yellowtail (supposed to be crab stuffing.) The fish was perfectly cooked and the stuffing tasted like stovetop (which I am a big fan of) with a little hint of crab, I would have liked more crab and more crab flavor for $18 but the dish was still wonderful and incredibly homey (think Keys comfort food). I especially liked the lemon sauce that topped off the dish.
Jason ordered the stuffed yellowtail (supposed to be crab stuffing.) The fish was perfectly cooked and the stuffing tasted like stovetop (which I am a big fan of) with a little hint of crab, I would have liked more crab and more crab flavor for $18 but the dish was still wonderful and incredibly homey (think Keys comfort food). I especially liked the lemon sauce that topped off the dish.For dinner I had the conch sandwich and this was the only dish I was not impressed with at this restaurant. The conch was tough, the coating too thick and a bit greasy. I would not order this sandwich again but would order anything else on the menu.
This is a pic of the conch chowder I had for lunch at Herbies. I loved this dish, very fresh, a little spicy and wonderfully clean tasting (all the ingredients can stand on their own but mix together beautifully as well.) Jason had a burger (no pic) that was amazing as well!
Herbies makes the best key lime pie I have ever had! It was amazing, much better than the Blonde Giraffe which won the key lime competition.
We also ate at Keys fisheries in Marathon. We ordered the stuffed lobster (crab stuffing), coconut shrimp app and grilled yellowfin sandwich. All the food was good but the shrimp was definitely the standout for me. The lobster was a bit tough (overcooked) and the sauce they topped it with (brown gravy) was not the sauce I would have chosen to accompany this delicate dish but at $15, it was still a great deal.
Here's a pic of the coconut shrimp. These had a sweet mango and horseradish sauce to accompany that really complimented the shrimp and the coconut.
Jason and I had our own grilled dinner at the amazing resort where we stayed (Valhalla Point). We grilled fillet steaks and zucchini and made grilly potatoes (Liz' recipe with old bay onions and butter) had Key west pink shrimp and fresh sliced tomatoes. Washed it all down with a Red Stripe...and island dinner for 2 happy travelers.
Steamed shrimp J made on the grill. 
We also ate at a local fish market called Fish Tales. I ordered the mahi with salsa fesca (a lot like a spicy Uruguayan chimicurri) and J ordered the sliders. Both meals were good but neither impressed us enough to return.
Jason's sliders.
We fell in love with the food, the scenery and the layed back lifestyle of the keys. Key West was a bit too crazy for us but we loved Marathon and especially Valhalla. Ours was the perfect relaxing vacation in the keys. I snorkeled, layed out on the beach and even went chumming for shark with J (thank goodness he didn't actually catch any!!!) J caught a tarpon on fly (life long dream for him) and was able to reconnect with his childhood. We both saw some of the most beautiful sunsets in the world and had a chance to wish upon a shooting star. We reconnected, we ate, we had fun and now we have the memories to last us the rest of our lives. Will we be back? You can bet on it!
