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Seeing as I got to the island in 1965 when I turned zero, and took off when I was a still a kid, I think the insights I list below might be worth checking out if you welcome trodding off of the beaten path.
[UPDATE 07-07 - I am now a vegetarian, after learning that giving up meat reduces an individual's carbon dioxide signature by 55% annually. For future reference.]
UPDATE 07-08: I added Eden House to my list.
It hasn't changed for 12 years. It's an oasis. Most people who go here understand what good food really is. Good food ainn't - that's ain't not - ainn't fancy. Good food feeds the soul. Fish sandwiches made from fresh fish and fresh bread from here actually brought in by the owner, Buddy, and by Buddy's own buddies is good food.
B.O.s looks everybit like a ramshackle roadside fishhouse because it is. My granddaddy, Walter"Tete" Newcomb, took me to these kind of places all the time growing up, and preferring 'em stuck, I guess. Even after traveling half the globe, I still come back here, and the fresh-cut french fries just make me feel special. Like I belong.
Personally, I feel that B.O.'s has the best hamburger on the island. It's served on Cuban Bread, and it's big and if you say you "want the Special," the terrific homemage fries are included free in the deal - sort of a mutual "wink, wink" for regulars and "people in the know." (And it's true- free fries just for saying, "the special, please!")
Buddy and I know each other from sight. I bet the only tow words he and I have said to each other in the past seven years is "Hey Bubba," but we both know who the other is. And that's why I like him and Holly's place. They're real. The people who work there are real. They have their own lives. They feed people the food I like best. And because all us neighbors here on the island really do get excited when the grouper comes in. The news goes straight down the Coconut Grapevine!
B.O.'s AIN'T pre-made, pre-cooked, pre-flavored, or Sysco Food's brand.
B.O.'s IS B.O.'s, and that is off-the-grill, money-where-your-mouth-is localized greatness. "What's not to like?"
BTW, best conch fritters on Key West proper. Some say best in the world. Plus homemade fresh limeade. What's not to like?
SPECIAL NOTE, for appreciators of gastronomy : The Chili Dog is actually miraculous.
Dennis' Pharmacy was an island mainstay for twenty years, and the home of the ORIGINAL Cheeseburger in Paradise. The Esperanza Family has cooked at Dennis' for over fifteen years. On the original menus, there was an admonishment to let all the famous people jsut sit there and enjoy there meal. And it was serious! About a year ago, the original Dennis' closed. It was a big deal. (The building became a bank. Wow.) But the family was dedicated to re-opening as soon as they found the right location. Well, guess what? They found it. In Bahama Village, at the equally-renowned Henrietta's Art of Baking, on Petronia Street. (Famous for her home-made coconut strips, regular or chocolate-dipped!)
So. Because it is in Bahama Village and looks like someone's kitchen, traffic is limited to the determined, care-free, and open-minded...and locals. It's a breakfast and lunch destination, plates and flatware are all disposable. And they serve a dish which is deep-fried picadillo in cuban bread. It's AMAZING.
Like I said, it's all local. Only the very brave venture in here, just because it looks so unusual on the inside. But the food and people are the best.
UPDATE 12-07: Henrietta's has moved, and now the entire establishment is Dennis' Pharmacy, an amazing diner serving very affordable and tasty home-cooked Conch-style, Cuban-influenced breakfast and lunch to 3:30 PM Monday through Saturday.
There are few restaurants I can praise as highly as Mo's. Not anywhere in the world. It is Haitian-owned and the family of five operates it together. There are children here regularly singing or studying or helping, and the experience is refreshing.
However, it is the food on which Mo's must be rated and regarded, and as someone from here who has had the opportunity for travel and experience I can say without hesitation there is no more flavorful food on Key West or anywhere from Key Largo on down. Even the lemonade and ice teas are something special!
Some food is spicy, some is tame, but all carries the trademark flavors which bring in the regulars such as me, and chase away the phony.
To be clear, Mo's Restaurant is not Margaritaville, Half-Shell Raw Bar, or Capt. Mario's Seafood Buffet. It could not be; it is GOOD!
There are many corners and spots on Key West that only the true of heart and rich in spirit have ever been able to discover. Mo's Restaurant is not only where you would find Tennesse Williams, Ernest Hemingway, or Captain Outrageous, it is more than likely where those who follow in the same footsteps can be found now.
Recommended: Anything with fish, beef, vegetables, seafood, or sauces. I myself order pasta every other time, or twice a week.
This is the place for the best best BEST conch fritters on the island - only it isn't on the island, it's on STOCK Island, which is sort-of Key West, but not really. Getting there is half the battle. But it's actually simple. "Leaving" Key West, t's just off of Highway 1, take a right onto MacDonald, then a right on 5th Street, then a left on 5th Avenue. Macdonald, right on 5th, left on 5th. Across from the baseball field, on the left, there is the Rusty Anchor. And MY GOD IS IT GOOD! This is how seafood is supposed to be prepared in Florida. You can have it anyway you like. It's all good. But like I said, the conch fritters are just exactly like my grandmama would make for me every Saturday night. Fat, fluffy, delicious. Like pieces of heaven. If you eat here more than once, you get some sort of extra-special credibility, like you obviously know what's what. BTW, when it's hot in the summer, the AC is cranked down to sub-zero. (FYI) Plus, the ice tea is real good, too.
This spot is off-Petronia, on Center Street, between Duval and Simonton, one block up from Duval, on the right. And it is a small little church thrift store in a large old wood single-story, white-painted building. And you probably are uninterested in such a place. It has a fine selection of books, strange clothes, bits and pieces of cooking ware and electronics, some house goods, and some toys.
The only thing is almost no one knows its there, and it is special in the true Key West kind of way. Fun fun fun.
Eden House exemplifies every aspect of what makes Key West exceptional and wonderful and "unique."
In other words, you have either got to have a good sense of humor, or you have to be able to appreciate one.
Here's why: Mike Eden surpasses "character" by several degrees?he is a genuine world-class Key West celebrity.
This man is patently intellectually brilliant, overtly outrageous, and alternately hilarious! Whatmore, his staff?who love the man (and the Guesthouse) dearly?do all they can to encourage him for the good of the operation. With a whopping 56% return rate (!!), obviously more guests agree with the approach than not.
Mike Eden (who naturally I have seen around the Island for a LONG LONG time, and even bantered with at a party or two) is one of those rare people who people genuinely either are put-off by or they love.
Either you "get Mike" and the whole Eden House groove, or else you don't. Sometimes it's the one and not the other. In any case, it's not personal, it's all in good spirit. And at Eden House, humor is not merely appreciated. It's PART OF THE SHOW! (Speaking of which, the "cheap liquor" has been an ongoing joke at the Eden House for eons. Once a guest commented on "being served the best Scotch of his entire life." Mike didn't miss a beat. "This," he lambasted, "is $12 a quart rum.")
As I have long understood and now am certain, the Eden House is a Key West treasure. It is one of the most outstanding guesthouses on the Island. Not to be confused with FINEST, rather more like FUNNEST. It is, as the the saying goes, "good for the show."
And if for whatever reason we are unable to extend our human longevity beyond the ordinary lifespan, my guess is that should Mike Eden ever decide to depart this mortal coil in a discourteous and ill-timed fashion, that the guests of Eden House will continue coming for decades afterwards without having to miss him at all because Mike's is the type of spirit that would linger. Not out of spite, mind you, but rather for not having finished saying what was on his mind!
In conclusion, IMO, Eden House is a Key West treasure, and long may its merriment reign!
If I had but one single thing to do in Key West, it would have to be visit the Mel Fisher Maritime Heritage Museum. For the record, it must be said that I love history, science, antiquity, research and narrative. By narrative, I mean "a good story." And most of all, as it should be, the museum dedicated to the work of Mel Fisher unfolds like a good story.
Walking in the doors for the first time, I would suggest one look around the imposing building first thing. There are surprises to be discovered there alone: Foremost, the mighty anchor which holds down the courtyard. (Not to mention a couple of quite taking piratical statues on the side.) Making your way through the doors, however, is one of my favorite aspects of this experience. For in walking in and having a look it would seem there the museum is just another over-hyped and underwhelming tourist experience. There is a gift shop (best saved for last) on the right, and a small movie showing room to the left. Inward is what look like a typical "lo-tech" attraction setting: Walkway, placards with information, dramatic lighting on underwhelming display, etc. But after passing through this short bit of seeming fluff one comes upon THAT UNBELIEVABLE IRON CANNON, and from there it is as if a doorway or portal to a wayback machine has opened up.
Study the details of everything. It is the intact collection of a moment which occurred some 400 years ago, and by a monumental and disasterous act of nature was captured some 60-feet beneath ocean to be almost lost in time except for the faith of one man, Mel Fisher. For 16 years to family friends and supporters, he recited his now-famous mantra, "Today's the day!" Then, one day, in fact it was!
The artistry and craft in the simplest tools is evocative. There is a nearly tangible connection to those who handled, owned or operated all of it. Even the ballast stones tended by seamen and enslaved people radiantly bare the imprint of their handlers. The preserved basics and staples do not pale in comparison to the treasure, they illuminate it.
And there is treasure. "I lifted a gold bar," the admittance sticker proudly proclaims, and you will! So too will you be in the presence of finery, jewelry and refinement of a craftmanship which is so far removed from our modern understanding of manufacuturing processes as to give it and everything a glow of otherworldliness. In bringing up the treasure and displaying it with such obvious genuine respect and admiration, the Fisher family has given the spirit of the historical dead a living home in which to reside. As I said, for those who pay attention, a real feeling of historical presence is tangible. The building is not haunted but it is certainly occupied!
And this is all on but the first floor! There is more treasure, more story, and another shipwreck on the second floor: The Henrietta Marie slave ship and attending story! Take your time, stroll without rush, and read over and examine the materials present at every turn and every step here as well. The Museum is no hokey-jokey time-filler. Rather it is a place empowered by a passion for research and history which resonates with the modern world by announcing to all comers: "We were here! We existed! We had lives! We had dreams hopes aspirations! And we were real! WE WERE REAL!"
The Mel Fisher Maritime Museum is found nowhere else on the planet besides Key West. It says as much as our history as it does about our future—we too will have had our day in a future time—and for those reasons as well as I have described above, not only do I recommend it above all other attractions the island has to offer, I recommend in seeing the Museum one be open to something special. For it is here!