Key West is a touristy town, and dining experiences in such places often run the gamut from great to poor in a way that normal towns don’t quite see.  The touristy places attract some top flight restaurateurs and chefs, but also have an unfortunate number of spots living off their location and banking on glitzy advertising, high traffic, and reputations that may no longer be earned.  In my Miami Beach years, I often made the point to visitors that the absolute top tourist area, Ocean Drive on South Beach, definitely fit into this latter category and the restaurants there could not compete with those on, for instance, Lincoln Road (also on South Beach) or Wynwood on the mainland just across the causeway.  I am years out of date for Miami Beach recommendations, and your mileage may vary, so I only use it as an example.

Sunset at Sunset Lounge

Our experience in Key West, however, has been quite good and often excellent, with very few places that we would recommend against.  Part of this is our online research, part of it is freely offered opinions from our many friends in the area, and another part is that this was our fifth winter on the island (on top of the numerous visits made before our fulltime RV days) and so we know, to a large extant, what we like and what we don’t here.

Old Town Mexican Taco Tuesday aims for higher end tacos at a higher price than Lucy’s

This year we resolved to “eat out smart,” i.e., select our restaurants carefully, don’t get pressured into going to those places we didn’t fully appreciate in past years, and hit some new, well reviewed spots.  In our last post. about the the many social events we attended while in Key West. we covered Taco Tuesday at Lucy’s, Wing Wednesday at the VFW, the Sunset Lounge on the naval base, and Mangrove Mama’s on Sugarloaf Key.  I won’t belabor the point on those except to reiterate that Lucy’s taco day is better than Old Town Mexican’s (and there upstairs bar is great any day of the week,) the VFW (in partnership with Treble Hooks) is truly a great “bang for your buck” option (especially if you’re drinking,) Sunset Lounge provided a mixed bag, and we are willing to give Mangrove Mama’s another go before passing final judgement. 

So where, other than those four, did we dine and to which of them do we give our highly coveted endorsement?  Let’s start with the happy hour specials at The Boat House.  Get there early or expect a wait, but it is well worth it.  Basic drinks and all the “small plates” are half price.  Fried lobster, lamb chops, filet mignon and mushroom skewers, multiple shrimp options, baby back ribs, and much more all at half price.  We find that three items is more than sufficient for each of us, or just two if we split the less than $2 Boat House chefs’ bread.

Steve and I at The Boat House

El Mocho is the best low cost Latin restaurant in the Lower Keys.  Let me repeat that: El Mocho is the best low cost Latin restaurant in the Lower Keys.  I will stand by that against any competitor.  It is authentic Cuban fare at rock bottom (for The Keys) prices.  We loved swinging in for tostadas (Cuban bread toasted, buttered, and flattened,) empanadas, or pastelitos de carne (pastries with flavored ground beef inside.)  The highlight of our multiple food experiences there, however, was the Friday special: oxtail stew.  Aside from being delicious the serving size, which included toasted bread, maduros (fried sweet plantains,) white rice, and garbanzo beans, was more than sufficient for Rose and I to split.  We waddled out of their full, with leftovers, and only $15 poorer.

Somehow we never got a picture from El Mocho, so enjoy this excellent shot of Deb and Steve.

We attended a fund raiser at the historic Key West Fire House Museum, and ended up winning a silent auction for t-shirts from The Lobster Shack restaurant.  What can say, Rose liked the design.  When we picked them up a week or so later we went straight to the shack wearing said t-shirts, and I had a fantastic Maine style lobster roll while Rose enjoyed a delicious shrimp roll in the same style.  It’s a tiny little place but we thoroughly enjoyed it.  Next winter I might compare their lobster roll to another place that comes highly recommended, but for now I would not hesitate to recommend The Lobster Shack.

Let me take this opportunity to rant a bit about crappy Tripadvisor reviewers.  I am in the habit of checking out not just the general assessments on that site, but I tend to read the worst reviews even when they are in the distinct minority.  Check those for The Lobster Shack: One guy gave them a one star review because they closed early after the death of an employee’s father and a high wind advisory.  Another gave one star because, essentially, he didn’t understand the difference between Maine and Florida spiny lobster.  A few other two star reviewers likewise did not understand the difference between these two distinct crustacean species, and were thus dismissive of the Maine lobster prices here in a place more than a thousand miles from Bar Harbor and Kennebunkport.

The Upstairs “Locals” Bar at Lucy’s es quite nice.

Last year we had a fantastic, serendipitous seafood pasta meal at Rustica, with liberal amounts of hogfish, shrimp, and other offerings from the sea.  We did not manage to get back on a day with that special, but the pizza was top notch, though “artisinally” priced.  Next year we plan on checking their schedule so we can once again enjoy the delicious seafood pasta.

Roger, Stan, Marilyn, and Barny in the backgroud.

Angelino’s Pizza is another iconic downtown Key West establishment that we have patronized and loved during various bar crawls.  The individual slices there are about as great as you could hope for, particularly during an evening of morally questionable activity.  The actual whole pies, however, we found woefully lacking, as did a couple of our friends during separate visits.  Bottom line: slices yes, pies no, and we will remain a bit suspicious next year even for the slices.

We loved the amazing Sunday brunch at Bistro 245 so much last year that we did it twice.  We felt that to be a bit glutinous, and thus resolved to only do it once this season.  It did not disappoint!  Once again we went with our good friends Steve and Deb.  Located in the Margaritaville Resort in front of one of the cruise ship mooring piers, we love the outdoor morning view, excellent service and incredible and varied buffet offerings.  Yes, it is $44 per person, and thus our most expensive meal of the winter, but with the bottomless mimosas and champagne, imaginative food options, fantastic lamb and prime rib, raw oysters, sushi, omelet station, smoked salmon and cream cheese, crab claws, to-die-for desert section, and a dozen other things I won’t list, we found it well worth the price of admission.  Besides, we won a silent option at a Habitat for Humanity fundraiser that covered the tax and tip!

Two Friends is one of Rose’s favorite, nostalgic, Key West spots.  It has great environment with a top quality roster of live music acts performing at a volume that is not overly intrusive (unlike the horrific Kelly’s Irish Bar, just to pick one example.)  We paid a pretty penny on our Saint Patrick’s Day visit for Rose’s snow crab legs (obviously a traditional Irish meal,) my spicy chicken wings (common fare in County Kerry going back centuries I understand,) and a stream of drinks ($5 Jameson’s) but it was thoroughly enjoyable. 

Some of our Sigsbee friends raved about the gigantic fish sandwich from Mundy’s Pirate Seafood, a little shack of a place in a strip mall in the center of the island.  We remembered buying shrimp from the colorful owner at a craft market downtown last year, and gave it a shot.  The reputation he enjoys is well deserved; it was a huge and tasty fish sandwich with a mound of fries.  We split it and were completely full.  While trying to find the place I noticed that his google search results provided an old and “permanently closed” location.  I talked to him about this, got his correct address and hours, and fixed most of the google results such that you get the right address and correct hours, however the google pin point drops on the old location.  If anyone knows how to fix this, please let me know.  It’s even worse with his Tripadvisor result, which shows him as closed.  I would like to fix this as well, so any recommendations appreciated.

Didn’t get a pic of Mundy’s either, so here are the wings from the VFW.

Near the end of our stay we enjoyed a flight of beer and a burger from Waterfront Brewery.  I am surprised it took us so long to get there given that we are quite into trying out local small batch breweries.  It was solid, and since we went for happy hour, quite affordable.

This sounds like quite a lot of restaurant activity for people supposedly on a tight budget.  We greatly mitigated the costs, however, by usually only dining during the happy hour or daily specials, and by making extensive use of the many discount cards available at certain kiosks.  Many of them are Buy One, Get One for drinks, but others offer half off appetizers or some other discount.  So yes, we ate and had drinks out quite a lot, but we did so pretty affordably, and look forward to more next year!