Key West

I’d always been curious about the Florida Keys- especially Key West. In fact, I remember the first time I heard about them. It was about ten years ago, and my dad and I were watching the 1948 movie Key Largo. It’s based on a play of the same name and stars Humphrey Bogart, Lauren Bacall, and Edward G. Robinson. You should definitely watch it, because it’s an absolute banger. It made a deep and immediate impression on me of the Keys as being a very distinct- even mysterious- region. One of the few places in the Eastern U.S.A that still has the feel of a frontier. A remote hinterland, with its own customs and its own pace of life. A place so small you could quite literally miss it when perusing a map.

The Florida Keys are a chain of extremely small islands that extend into the Caribbean Sea off of the southern tip of Florida. Key West is the last island in that chain. There’s a massive highway that runs the length of the islands and connects them to the mainland, and it’s supposed to be the most surreal road in the U.S.A. The highway ends at Key West, so being there you have the sense that you are at the extreme limit of America. In fact, Key West is the southernmost city in the contiguous United States. It’s closer to Havana, Cuba than it is to Miami.

One of my all-time favorite writers, Ernest Hemingway, adored the island and lived there for many years in a house that now exists as a museum to his legacy. It’s a place I’ve wanted to make a pilgrimage to for many years, the same way I have with Thomas Wolfe in Asheville (NC), John Steinbeck in Salinas (CA), and William Faulkner in New Orleans (LA). I still thought Jamaica would have been more fun, but as far as replacements go, Key West was pretty good for me personally. It was already a place of great interest to me, and probably the spot in Florida I was most eager to visit. In fact, it was probably in my top five locations in the U.S.A I most wanted to visit at that point, and so the surprise announcement that I’d now actually be seeing it was something I became quickly excited about.


I’m also determined to try and see all 50 states before I kick the bucket. The idea that I’d get to spend any great deal of time in each is a fantasy, as travel is very expensive and at the moment I wash dishes for a living. I’ll take what I can get, just to say I’ve stepped foot in each state. And so I was more than happy with an afternoon in Florida. I didn’t think for a second that I’d be scratching another state off of my list this year. This would be number nineteen; The Sunshine State.

I wondered if this meant that Key West would be more exotic for me than my travel companions, who would be setting foot on their own soil. Each of them had been to Florida before. Anne-Marie had just two weeks ago flown out to Miami for a weekend conference. Aaron recalled going to Seaworld as a child, and Ted and Sylvia had been there just a couple years ago for a Billy Joel concert and some deep sea fishing. But there’s a reason Florida is one of the most-visited places in the entire U.S.A; there’s just so much to see and do. And none of my Americans had been to Key West before, which, as I said earlier, is far removed from the mainstream American experience. After all, we were now within pissing distance of Cuba, so this part of Florida would have a distinctly Caribbean flavor.


The Freedom docked at a U.S naval base and as we tried to exit the ship we discovered that for some asinine reason we had to have these shore pass tickets in order to do so. It wasn’t very well explained and when we tracked down the place where the tickets were handed out, there were no tickets left. We’d have to wait around for an hour until they got new ones- an hour of precious excursion time. I was a little irked by it because I hate unnecessary layers of bureaucracy. They scan your Sail Cards when you exit the ship anyway, so adding another thing on top of that in the form of shore passes seemed like the definition of “faff”. My friends took me to the Rum Bar on Deck 9 and calmed me down with a Sangria Swirl. Yum.

Half an hour later the Freedom scrapped the whole ticket thing and said that all passengers could now fuck off if they wanted to. Huzzah! When we entered the ship for the first time at Galveston, we did so at Deck 3. Our first glimpse of the Freedom’s interior was its most impressive area- the gorgeous Atrium. It looks like Rapture from Bioshock before the shit hits the fan. This time however, we were exiting the ship from Deck 0- its lowest level. Decks 1 through 11 are the decks meant for passengers, and they all have that lovely Art Deco vibe. Deck 0 was like that Forbidden Corridor from Harry Potter, a place full of secrets meant for staff eyes only. So it was kind of interesting to go down there, if only briefly. It’s white, metallic, and functional- like a hospital. As we passed by a plastic curtain that led to the ship’s infirmary, my mind raced with possibilities of the ship hiding something sinister from us. Experimenting on passengers or something.


Anyway, we quit the ship and Casey Jones’d it out of the naval base on one of those mini train things you see at theme parks packed with screaming children and dads with right-angles in their backs. We weren’t allowed to take pictures until we left the military base, so we passed the time making idle chat with the driver and waving at the nice fellows with guns.

Key West is tiny, by the way. You can walk from one side to the other in 15 minutes at its widest point. It was also baking hot. This will probably sound stupid, but I was taken aback by how hot it was. I figured it would be warm but not too hot, it being the first week of March. Back in Texas, where we had just two days ago set sail, it didn’t feel like summer. But here it felt like mid-July for some reason. I didn’t get it. After five minutes of walking down Whitehead Street I could feel droplets of sweat sliding down my ass.


I got the impression that Key West was a place that remained unchanged the year round. The streets were packed with tourists. I asked a tattooed local shopkeeper what the summers were like. It was a little hard to concentrate because she was wearing a strapless bralette that looked like it was being stretched to bursting point, but she said something like “It’s exactly the same all year.”

It really does seem like a place that exists in its own time and space, untouched by the rest of the United States. The little island of perpetual summer. The streets are all lined with heritage buildings and there’s nary a drab brick office structure in sight. It’s all Victorian Conch Houses with gleaming white facades of horizontal clapboarding and double-hung sash windows. Verandas, rocking-chairs, balconies of potted plants. Everything in the shade of densely-packed lines of palmettos. No structure seemed to be above two stories in height. The people that lived here seemed proud of their little paradise- and rightfully so.


We enjoyed dipping in and out of the various historic bars and mom n’ pop stores. The overall vibe of the town reminded us strongly of Fish Creek, WI. I had an image of the people that lived here as waking up whenever the hell they liked, going fishing, and languidly retiring to their porches where they’d drink rum in their rocking chairs. They’d know the habits of the tourists as well as the whims of the sea. They defied the pace of modern life and prioritized their sensual pleasures. They surfed, fished, got drunk, ate well, and fell into bed easily with whomever they pleased.

Our first stop in Key West was the fabled Hemingway House. On the way there I remembered with dismay from all the pictures I’d seen that it seemed enclosed by a wall of trees. This was true. We got there and the line went all the way down the street. I wasn’t interested in getting a tour, especially given that it was so hot and we had just a few hours of exploring afforded us before we had to return to the ship. So I snagged a few pictures with my camera, wishing I could have gotten closer like I was able to at the other Hemingway house in Oak Park, Chicago, before we moved on.


The walk south wasn’t in vain however, because we happened upon a lil place called the Lobster Shack for a much-needed rest. The fella that owned it was the real M.V.P, because he was so friendly and he had the freshest lobster this side of the Mason-Dixon Line. He was also extremely laid-back, despite how busy it was in there.


I got their signature lobster roll, the Key Lime Lobster Roll, and it was so damn good. It was then that I realized for the first time that Key Lime Pie originates from Key West. You’d think I’d have figured that one out sooner; it’s in the name after all. I’d always figured that limes were the less-mainstream, hipster alternative to lemons- the Luigi to its Mario if you will- but on the island of Key West it reigns supreme. From what I could tell it was one of two icons for the island. The other being roosters. Don’t ask, I have no idea why. But roosters are to Key West what pigeons are to the U.K. They roam the streets freely, pecking at random stuff, cuck-a-doodle-doo-ing at nothing in particular. No one monitors them or questions their presence. If anything, they are revered. The locals build monuments to these ancient creatures, great murals and edifices to their majesty. One bar in particular was plastered with various paintings of roosters, and they were all headshots, so they seemed like they were kings or presidents posing for professional portraits. It’s fucked up, man. But the rooster is a respectable icon as any for worship, so fair enough I say.

We stopped off next at a bar and brewery called First Flight, so named because- I shit you not- it’s the birthplace of Pan Am. The first tickets for Pan American World Airways were sold right out of this little old wooden building in which we now sat. I ordered a Key Lime Martini and we sat at the outside bar, enjoying the shade of the canopy, the lovely view of the walled garden, and acoustic covers of “Layla” and “Sweet Child of Mine” by the live musician. This was easily my favorite part of our day in Key West, and one of my favorite parts of the cruise as a whole.


The last thing we did before returning to the Freedom was chill out at this street beach we found on the north side of the island. The water was freezing when you first touched it, but once I’d waded in far enough that it reached bollock-height, I realized that the worst was over and committed to submerging myself fully. After that it was really nice. I kept telling my companions that you didn’t feel the cold once you were submerged, but I don’t think they believed me. It was so hot that I couldn’t stand to be anywhere else except the sea at that point, so I just floated in the water and tried hopelessly to make eye contact with Aaron and Anne-Marie like a small dog trying to implore its owner to get off the couch.

Before long it was time to head back, and so we bid the beach goodbye. We left a few minutes early so that we had time to grab some key lime milkshakes and ice cream before we caught the shuttle-train. A wise decision if ever we made one.

Discussing our time ashore, we concluded that Key West was indeed a most agreeable place. We could all get down with the sunshine, the fresh lobster, the key lime in everything. I wouldn’t say any of us left with a burning desire to go back, but we certainly enjoyed our time in “The Conch Republic”.

Conch,” I whispered to Aaron. “Sounds dirty, doesn’t it?”

“Shut up,” he said.

And thus, our first port of call had ended.

2 Replies to “Key West”

  1. I would love to see where Hemingway lived and also try the famous key lime! He’s still one of my favourite writers and after living in Ireland for nearly two decades I would like nothing more than to bask in neverending sunshine. Thanks for sharing and have a good day 😀 Aiva

    Liked by 1 person

    1. Thank you for your kind words!! You should definitely go, it’s a lovely place with a great atmosphere 🙂

      Liked by 1 person

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