Travel Magazine

Visiting Key West

By Conroy @conroyandtheman
by Conroy

Visiting Key West

A view along Duval Street

Key West. What comes into your mind when you read those words?
How about a sunny tropical island? Key West is the only American city never to record a frost. Its warm climate, flat geography, and native flora are closer to that of the Bahamian cays than to the rest of Florida (let alone the rest of the continental U.S.). Walking slowly down busy Duval Street under the fierce July afternoon sun and through the still humid air, sweat seeping from your face and torso, you realize that Key West, unlike any other place in the U.S. is truly tropical.
What about a quirky laidback end-of-the-line town? Some of the locals call it Key Weird and the city has a long reputation for openness; Cuban immigrants, homosexuals, those just looking for a place to forget the past to start over, not to mention the hordes of pleasure seeking tourists (to name but a few groups) have given the island its own distinctive come-as-you-are and do-as-you-please culture.
Or maybe, if you’re geographically inclined like me, you think of the southernmost city in the continental United States? Let’s start with that. For those who haven’t been, Key West is the last island in the long chain of the Florida Keys, the archipelago that stretches in a hundred mile arc west-southwest from the southern tip of the Florida peninsula. The Keys rise from the shallow turquoise waters of the Straits of Florida and range in size from small, flat, forested islands to tiny coral specs. Key West city occupies the small Key West Island, which is just five square miles, as well as a few neighboring islands to the immediate east and north.
Visiting Key West
It’s hard to fairly distill a place in a brief description, but perhaps one famous landmark will help. Take a look at the photo on the right. This is the famous concrete bell at the intersection of South and Whitehead Street that marks the southernmost point of the continental United States. This bell makes for a great photo op and what you can’t see is the lengthy queue of people that are usually lined up during the day to get their pictures. Let’s linger on this monument for moment, and consider the four separate messages contained in its 18 words. They tell us a whole lot about Key West, or about how Key West wants to viewed by the outside world.
This is by far and away the Key West’s most celebrated claim to fame. It is the southernmost city in the contiguous U.S. Quick quiz: can you name the eastern-, western-, or northernmost cities in the continental U.S.?1 Probably not, but you may know about Key West because residents have made the most of their geographic extreme, it’s part of Key West’s allure as an end point, the end of the road, mile zero, the furthest you can go. The thing is anybody who stands by this monument can see that it’s not actually located at the southernmost point on the island. The real southernmost point is just to the west on the U.S. Navy’s Truman Annex property where the general public can’t go. And this is a nice microcosm of Key West itself: almost the southernmost place. Key West is an island far from Florida’s mainland, so it really isn’t a part of the “continental” U.S. at all. I would suggest it’s more accurate to say that Key West is the southernmost point in “lower 48” states or even the contiguous U.S. Terminology aside, all of the uninhabited Dry Tortugas (islands that are also part of Florida) lie to the west and several to the south of Key West2. So technically, Key West isn’t the southernmost point in the “lower 48”. It’s just the southernmost point that’s easy to get to.
And of course, it’s worth noting that all (or just about all) of Hawaii is farther south than Key West, and for that matter so is Puerto Rico, the U.S. Virgin Islands, and almost all of America’s Pacific territories. Why am I harping on these technicalities? I mean who cares really?  It’s just this: the idea of Key West as the southernmost point in the U.S. – as a geographic extreme – is critical to the culture and atmosphere (and even the psychology) of the place. It doesn’t have to actually be the southernmost point, it just has to seem that way. Which leads to the next phrase.
Like the southernmost point, “90 miles to Cuba” is a well-worn phrase, and it’s more or less true (though in fact at the closest point Cuba is a little more than 90 miles to the south). Key West is significantly closer to Havana than to Miami3. And this phrase became commonplace during the Cold War and especially the Cuban Missile Crisis when Soviet nuclear weapons were being installed “90 miles” from the U.S. But what’s the big deal about this fact? I mean Bimini in the Bahamas is only 50 miles east of Miami. Monterrey, Mexico, and Toronto, Montreal, and Vancouver, Canada are all closer to the U.S. border. I think again, like the southernmost point, the idea that exotic Cuba is seemingly so close, just over the southern horizon, is important to the atmosphere of Key West: a place so distant and distinct from the rest of America that it’s like a foreign country.
And this may be hard to believe, but a few times as my girlfriend and I walked in the evening twilight, in and out of colorful shops, past raucous bars open to the street, under the darkening silhouettes of cruise ships that towered over dockside buildings, hearing many non-English voices, with the clinging, unrelenting heat, and wild palms trees and tropical vegetation overhanging the sidewalks, I did indeed feel, if only for a moment, that I was in some other country. A semi-America; not quite foreign, but disorienting and unfamiliar. Then something very American, like a loud pickup truck or the bright lights of a convenience store, would jolt me back. I was in America, Key West America, but America.
Visiting Key West
As you stroll around town, along busy Duval Street or through the quieter neighborhoods, you see a strange looking flag hanging from awnings, draped over balconies, and occasionally up flagpoles. A dark blue background, with a stylized sun at the center overlain with a conch shell, the word words Conch Republic wrapping around the top of the sun with the date of 1828 or 1982 in upper right (depending on the flag) and the two constellations on either side of the sun. Underneath the sun on some of the flags is the sly motto “we seceded where others failed.”4 This is the flag of the imaginary Conch Republic, which for citizens (known as Conchs) comprises all of the Keys and has its spiritual capital in Key West.
It’s all very tongue-and-cheek, but it had its origin in genuine frustration. In the aftermath of the 1980 Mariel boatlift, where Fidel Castro expelled 125,000 Cubans, and increased drug trafficking through the Keys, the U.S. Border Patrol setup a roadblock on the Florida mainland that stopped all vehicles from the Keys. This caused persistent major delays and was perceived by residents as imposing a hardship, or at least a major inconvenience, on travel and the Key’s tourist-fed economy. So in April 1982, fed up with the ongoing “blockade”, Conchs declared their independence and the establishment of a new nation. The ensuing publicity was enough to eventually have the Border Patrol roadblock removed, but the Conch Republic has lived on. It may exist now mostly as a gimmick, but it’s another manifestation of the separateness that Conchs feel. Every April Key West celebrates its “independence” with a week-long festival. Perhaps it’s just another excuse to party, but it’s something that belongs only to Key West.
And what does it mean to belong to Key West? I asked this question of Zach a young bartender as I sipped a mojito during a quiet afternoon. He came to Key West a few years earlier after college (it was unclear if he had actually graduated) and referred to himself as a local. To my understanding there are long-term locals who are labeled “saltwater Conchs” and newer locals who are labeled “freshwater Conchs”. I wasn’t sure if Zach’s residency was long enough to qualify him as freshwater or saltwater. But in any case, his reason for coming was twofold, the weather which was far more attractive than his native Ohio, and the laidback pace of life. These are two of the four reasons I can see for locating in Key West, in no particular order: weather, a slower pace to life, a freedom to live as you please, and an escape from whatever your life was before. In other words, it takes a certain personality to live in Key West. Fewer than 25,000 people call the city home, but those 25,000 live tightly together, sharing the same reasons for being there. Over the last several decades the number of families living in Key West has dwindled from more than 40% of the population to less than 20%. The average age has risen to 39, much older than the national average. Is it too dramatic to write that Key West is becoming and older, lonelier place?
If that’s true, then it’s also true that Key West is undeniably vibrant, just take a walk down Duval Street after dark or along Mallory Square in the hours leading up to sunset, but it’s an easy vibrancy. That’s not to say locals don’t work hard or that life lacks the expected edges. It’s just that in Key West, under the bright, flattening sun and ensconced in the perpetually warm air, far from the rest of the country, farther it seems than the slow four hour drive to Miami, life must be just a bit different. A different pace, a different perspective, and maybe different expectations. Life in the Conch Republic, different just like the locals want it.
The final phrase on the monument claims the sunset as Key West’s special attraction. Certainly the name Key West evokes the sunset; the west and sunset go together like island and sea. But this claim is yet another catchphrase to cast Key West as blessed by nature and the place to be to witness one of nature’s undeniable (if routine) magic acts. Come to Key West for the sun and watch it sink behind the western horizon.5

Visiting Key West

Mallory Square at sunset

If Key West has a center, or at least a focus of daily activity, it is Mallory Square, the brick and concrete paved plaza a little larger than a football field that fronts the Gulf of Mexico on the northwest corner of the island. It’s here that crowds gather each evening to watch the sunset and are entertained by street performers of varying interest and talent6, and local vendors/artists selling photographs, paintings, jewelry, trinkets, etc. Mallory Square is also at the center of the island’s port, situated between the cruise ship docks to the immediate south and the main marina to the immediate east. Along with the “southernmost point” it’s the most visited location on the island. The action at Mallory Square is concentrated in the hour or two before sunset and then mostly along the waterfront promenade. Watching the sunset is more than just a tourist activity, it’s part of the larger island culture. Locals gather atop the Concha Hotel, the island’s tallest building which affords a view overtop of Mallory Square and removed from the crowds.
The Real Key West
There’s certainly more to Key West than can be captured by 18 words on a colorful monument. I may have never eaten better than the meals I had there. I think it’s accurate to say that I had more Key Lime pie in four days than I had eaten in my entire life until then. Key West is also a surprisingly historic place. Since its founding shortly after Florida became part of the United States in the early nineteenth century the island has been a busy port at a strategic location. As late as the turn of the twentieth century Key West was the largest and most prosperous city in Florida, dwarfing nearby Miami; a fact that seems unbelievable now. But that was the overwhelming reason why huge sums were spent building a railroad and later a highway to connect the island with the mainland.
Its history is rich from the Seminole wars, anti-piracy campaigns, the Civil War, Spanish-American War, World War I and II, Cuban Missile Crisis, to the aforementioned Mariel boat lift. Then there are the interesting literary connections with extended residency of Ernest Hemingway and Tennessee Williams (to name but two). And President Truman treated Key West like a second home (indeed he lived in the Little White House) during his presidency. I doubt many people come to Key West for the history, but it’s fascinating and there to be enjoyed.
But these facets of Key West (except for the food maybe) are for visitors to enjoy, and there seems to be an irony to the many flavors that make Key West so attractive to tourists. The history, the setting, the people and atmosphere are the things that keep tourists coming and bring much of the money that keeps the local economy humming.
That’s really the combined message of the 18 words on the southernmost monument. Key West as a unique one-of-a-kind place to visit, from its geography, to its setting, to its character and people. Key West is populated by thousands of people who choose to live far from the rest of the country but that doesn’t stop them from inviting everyone else in.
1. The answers are: northernmost: Sumas, Washington; easternmost: Lubec, Maine (although Eastport, Maine is the easternmost community of any size); westernmost: Ozette, Washington (though Port Orford, Oregon claims to be the westernmost city on the U.S. mainland. Both of these places ignore Alaska, which of course is part of the North American continent).
2. Ballast Key is the southernmost island in Florida and the lower 48 states.
3. As the crow flies: 106 miles to Havana; 129 miles to Miami.
4. The others here can only refer to the southern states of the Confederacy who failed in their rebellion against the North.
5. But it turns out that watching a true sunset at Key West is harder than advertised. On our first night we watched the sunset from Mallory Square, but instead of seeing the orange disk sink into the sea, we watched it fade behind Sunset Key, a tiny island a few hundred yards offshore and northwest of Mallory Square. An unobstructed sunset can only be seen during the non-Summer months. The next night we were actually on Sunset Key for dinner but the tick clouds near the western horizon blocked the sun for the half hour before it set. Finally, we watched from the Concha Hotel, and again the sunset occurred behind the distant clouds. I wanted to see a mythical green flash sunset, instead in the “home of the sunset” I got obscurity.
6.For instance, watching a man juggle daggers with intimidatingly large and sharp blades while balancing atop an elongated unicycle tends to grab your attention, at least for a couple of minutes. While listening to an off-key rendition of “Knocking on Heaven’s Door” backed by what looks and sounds like a homemade ukulele is more likely to cause a quickening of the step to get the “performance” if not out of hearing range, at least well into the background noise.

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