9/7/2012 – The Original Margaritaville

The trip down the Keys from Key Largo to Key West was not what I expected at all.  Somewhere I’d gotten the impression that it was long stretches of steel & concrete bridges with nothing but aqua-blue water on each side.  Every so often you’d cross a key.  But it really wasn’t like that.  With the exception of Seven Mile Bridge, most of the keys are quite close together, some so close that, if it weren’t for the signs, you’d never know you passed from one to the next.  And the road was generally bordered by foliage of some sort, often hiding the water except when you gained the altitude of a bridge.  It was pretty and all, just not what I’d expected.  In places you can see what’s left of Flagler’s original railroad bridge the first connected the keys to the mainland.  Unfortunately, there are very few places to safely pull over and snap a photo except on the keys and then you’d just get a photo of surf shops and t-shirt shops.

We left Key Largo after breakfast at Mrs. Mac’s Kitchen whose motto is “Eat Well, Laugh Often, Live Long”.  I can buy that.

Took us about 2 hours to drive to Key West.  Just before we got there, we pulled over at a tourist information booth for a free map and to check in to the “motel discounts”.  The fast-talking girl behind the counter was obviously working on commission but she got us booked at the Southernmost Point Guest House for a price that seemed reasonable for what we expected to pay in Key West.  In hindsight, we’d have probably been better off to drive on in and take our chances but this was easy and our lodgings were right down at one end of Duvall Street, making our walking around plans very doable. Plus, they provided free off-street parking which, as it turned out, was a really good idea.

Once settled in, we headed out for our own self-guided tour of old town Key West.  We didn’t really have any destination in mind except to walk across the end of the island (the length of Duvall St.) which is about a mile.  Our first stop was just down the street from out temporary home: The Southernmost Point in the Continental USA.  We stood in line for the obligatory tourist shot.  Everyone was handing their cameras to the folks behind them in line to take their picture.  We took a shot of the folks in front of us and then they returned the favor.  I think that’s their Margaritaville Cafe gift bag in the photo because it definitely isn’t ours.

Only 90 miles to Cuba

From there we wandered along Duvall for a ways but quickly decided it was WAY too touristy and kitschy for our tastes.  If we’d wanted cigars it’d be different, Duvall would be the place to go with cigar shop after cigar shop offering their products.  But we weren’t interested in cigars or t-shirts with rude slogans or bikini bottoms with “Key West” written across the butt.  Instead, we walked a block south of Duvall, along Whitehead, where we came across the Hemingway house.

Unfortunately, unless you pay the $13 each for a tour, this is about all you get to see.  Maybe another time.

By now it was early afternoon and we were getting hot and thirsty.  We really wanted to avoid the tourist bars although we’re aware that with this being a tourist town, all the bars are more or less “tourist” bars.  However, we figured there must be someplace that is a little quieter and less crowded than the bars on Duvall.  We found just such a place at the corner of Whitehead and Southard streets.  The Green Parrot (“No Sniveling Since 1890”) is one of Key West’s oldest bars and is advertised as “where the locals go”.

We went in and ordered a couple of drafts.  The bartender wasn’t very friendly, not hostile, just not very friendly.  Probably a locals vs. tourist thing.  She was definitely chatty with the folks who looked to us like locals.  She was a lady in her late 50s/early 60s with the unlikely name of “Chicken”.  But the bar was pleasant.  It’s all open air, windows open to the street, but it’s cool and shady inside and the ceiling fans keep it nice and comfortable.  There were never more than 10-12 customers there at any one time during our stay although the place was big enough to handle tons more.  It was one of those places with about a jillion things on the wall to catch your attention.  After a beer and a stop in the adjoining gift shop, we got back on the trail.

Again, no particular plans other than to see Key West.  We wandered past lots of homes, large and small, snazzy and run down.


Some of the homes were built so close together that I can’t imagine how the second one was built.  There’s barely room to swing a hammer between them.

We eventually ended up on Duvall Street and saw the infamous Sloppy Joe’s Bar.

We briefly considered stopping in but, in the middle of the afternoon it was already loud and crowded.  The kind of bar where they serve your draft beer in plastic cups.  We opted to pass it by.  Just as well because later on in the evening we passed Captain Tony’s which advertises itself as “the original Sloppy Joe’s” meaning, presumably, that the other was not the place where Ernest Hemingway downed a few.  For the record, we also passed up Captain Tony’s as they had a live musician who was playing WAY too loud.  I said “HE WAS PLAYING WAY TOO LOUD!”  Couldn’t even begin to carry on a conversation.  No, instead of these two famous watering holes, we ended up at an unlikely place called “Tattoos and Scars” (“because every relationships ends up with one or the other”).  It was sort of a tattoo/biker bar but it was virtually empty, airy, cool, clean and, most of all, quiet enough to hear each other speak.  The beers were cheaper than at the Green Parrot, too.  We sat and sipped and ate peanuts in the shell and watched the people walk by the wide open doors.  This was a long building that didn’t extend back from the sidewalk very far.  The sidewalk wall was a series of wide-open doors making the transition from inside to outside pretty seamless.

By now it was getting to be late-ish afternoon and we started to think about getting something to eat.  Earlier in our wanderings we had passed a funky little place called the Conch Shop and we thought we’d return and check it out.  Rather than making a beeline for it, we decided to wander a bit more and get there eventually.

We were on Simonton at Angela when we stopped to admire a beautiful compound.  We assumed it was a hotel or mansion or something but it was surrounded by well-kept jungle.  While we were looking over the wall at the place, a guy came by and said. “Don’t stand out here.  Why don’t you go on in and take a look around?”  We thought, “Why not?” and followed him around to the entrance in Angela Street.  We balked when we saw the “Guests Only” signs but he insisted that it was fine so we continued to follow.  He led us to the pool area and the poolside bar.

The bartender, Barb, could not have been nicer.  Although having lived in Key West for a very long time, she was definitely not Chicken.  She was very nice and chatty.  We met a couple at the end of the bar from Kentucky.  After hearing what we were doing as far as living on the boat, they started to reconsider their living plans.  Probably won’t last until morning but at least we gave them something to discuss over dinner.  The next guy to come in turned out to be the editor of the local investigative newspaper, “Key West, The Newspaper” (“journalism as a contact sport”).  His name was Dennis Reeves Cooper and he was great fun to talk to.  He’s an old-fashioned liberal in the finest sense of the word.  Like my cousin Willie (a public defender), he enjoys tweakin’ “the man” when “the man” gets too big for his britches.  Of course, Dennis has spent the occasional night in jail as a result but he continues to carry on the good fight.  If we hadn’t stopped to admire the jungle around this hotel (whoops! forgot to mention that this place was The Garden Hotel), we’d have never met these interesting folks.

Refreshed, we headed out for dinner.  Fortunately I had marked on our tourist map where the Conch Shop was, otherwise we might have wandered for hours trying to find it again.  But, there it was, right on Petronia.

What had originally attracted us to this place was the menu on the sandwich board out front.  It showed conch fritters, conch chowder, conch salad, or all three together, as well as other stuff like “the Nasty Burger”.  We ordered the combination.  Unfortunately, they were out of conch chowder but the cook/waitress/owner said she’d give us extra fritters or salad.  We chose salad.  Unlike the conch we had on Key Largo, this stuff was quite flavorful, although not in-your-face flavorful.

The fritters were tasty and tender and not doughy.   The salad was conch, cucumber, tomato and jalapeno with some kind of subtle dressing on it.  It was really good.  Here’s a shot of the “dining room” and the owner/everything else:


I asked what made the Nasty Burger nasty.  She said that it was just so big and sloppy and juicy that it just gets all over your face and makes your face “all nasty”.  She assured us there was nothing nasty about how it tasted.

After dinner we wandered back to our room, dropped off souvenirs, etc. and then headed back out to Mallory Square for the obligatory sunset watch.  There were a ton of people there as well as buskers, jugglers, fortune tellers, guys who rode teeny-tiny little bikes, etc.  Did manage to get a decent sunset shot.


Finally, back to our room for a little TV before conking out for the night.  Had a great sleep but this guy or one of his relatives woke us up about 7:00.


I’d forgotten how relentless roosters could be once they started crowing.  There are chickens running loose all over the old town residential area.  Wild, I assume.

Had an excellent guest-house-provided breakfast (fruit, cereal, hard-boiled eggs, hash browns, sausage, toast, bagels, etc.) and now we’re ready to pack up and head back up to the mainland.


About sryoder

Steve & Lulu... retired. Had enough of the cold wet dreary fall/winter/spring in the Pacific Northwest. Bought a boat, fixed it up, sold our home and sailed to Mexico in November, 2010. Been here ever since except for occasional forays to the States (summer only, thank you) to visit the kids, parents and siblings. If you're looking for a sailing blog, this is the wrong place. This is a traveling, hunkering in, eating blog. Sailing is just how we get from place to place when we can't walk.
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4 Responses to 9/7/2012 – The Original Margaritaville

  1. Vickie says:

    thanks for the wonderful report! love the photos, colonial looking houses, food and Hemingway lore.

  2. Alan & Elizabeth says:

    Thanks for the last two blogposts. The Key Largo and Key West descriptions and photos are great. I’ve been missing my “Yodersafloat” fix.
    s/v Vivacia

  3. bud elkin says:

    You know that if you stop at the Marathon City Marina you would probably find two dozen or more sailors that read or have read your blog. It’s a hangout for all of us Florida sailors when we are in the keys. It has that Velcro touch to it. I will be back down this fall sometime. If you want to really see Key West in all its splendor, don’t go during pervertfest;; I mean Fantasy Fest in October. P.S. I don’t like the crowds and touristo places either. Enjoy the rest of your trip. Florida has lots to offer; you just need to know where to find it!

  4. Scott Wedge says:


    I have long wanted to visit the Keys. Not sure why, maybe just to see the lower right corner of the US. Anyway, thanks for the virtual tour!

    Has the climate down there got you thinking about doing some sailing in the Caribbean? Cooler than Sea of Cortez, yes? If you don’t mind the hurricanes….


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