A Little Nostalgia… A Portrait of Key West Culture, Then & Now

Last updated on May 11, 2023

I spent a decade of summers in my childhood camping in the Florida Keys with my family; the Keys were a mere eight hour drive from our home and our nine days of vacation were gloriously free as my parents kitted and fitted us five kids with fishing poles and snorkeling gear and reveled in the hours of kid-free time while we entertained ourselves.

My memories of grilled dinners, sandy swimsuits, and campfire chess games are tinged with the honeyed orange rays of long summer days and faded at the edges like an old photo.

Key West from childhood
Enjoying yummy grilled camping food with three of my brothers many, many years ago. I’m the one in pigtails. :-)
Sand Key Lighthouse, Key West
The Sand Key Lighthouse snorkeling spot is just off the coast of Key West, Florida and popular for pretty coral and brightly colored marine life close to the surface and easy to see!

As we grew up though, other summer plans, namely hanging out with friends, took precedence over family vacations and before I knew it more than 15 years had passed since my last visit to the Keys. And yet, my enthusiasm hasn’t changed; if you ask me about the Keys I wax poetic about the impossibly variegated turquoise expanse caused by shallow waters and miles of coral reefs.

The memories were sweet with the innocence of childhood and I yearned to go back for a visit, to beat back the uncertainty of nostalgia and instead confront the Keys as an adult. When James, a fellow travel friend from Chiang Mai, passed through the region I leapt at excuse to drive south and show off my home state.

The drive was altogether different, instead of five kids jumbling around the backseat (“mo-om, make him stop touching me!”) we had air-conditioned comfort as we left mainland Florida and started the several hour trek on the Overseas Highway to the southernmost city in the continental United States.

Bike Ride and Mural, Key West, Florida
A woman enjoys an afternoon bike ride near a beautiful mural in Old Town, Key West
The Strand, Key West, Florida
Conch Restaurant, Old Town Key West
Conch Republic license plate
They have a sense of humor down south and that cliche, relaxed island flavor

Within a few hours I was weaving the car through Old Town Key West, nervously navigating the non-car culture as bicyclists breezed by me traveling faster than traffic and pedestrians stepped off the curb with nary a care in the world as the sticky breeze blew in from the nearby Gulf waters.

Because we camped in the state parks throughout childhood, I remembered Key West only for the fire-breathing, sword swallowing antics during the Sunset Celebration on Mallory Pier, the drag queens standing in doorways as we slugged back to the car at night, and the overall amusement park aspect to our day-trips to the tiny island at the end of the chain of Keys.

Coming back as an adult was different altogether, I found Old Town Key West a vibrant city pulsing with tourism and though the locals were still quirky, everyone swirled together into a happy little medley so much more normal than my childhood memory.

You see, though Key West teems with tourism, the island is tiny and as often as I encountered other tourists on the streets, it was just as easy to chat up the sales clerks and cafe owners. Well beyond the ploy of appeasing the tourists, I found the locals incredibly willing to share stories and humor from the Conch Republic, the unofficial tongue-in-cheek name given to Key West when the “micronation” seceded from the US back in the 80s.

Conch Republic, Florida, and US Flags
The Conch Republic flag wave proudly in Mallory Square next to the Florida State flag and the US flag

Cafe owners shared coffee at the counters with regulars and the curious tourist (me) could sidle up nearby and casually drop into the open conversation with questions and observations about the town. In the evenings, the locals are just as likely to hit the pubs on Duval Street as the tourists and I found it pretty easy to prod a local into regaling me with uncensored stories as the night progressed.

The locals love their culture and Conchs (Key West born locals) are just a different breed altogether. I’m a native Floridian, rare enough in and of itself, but the local Conchs I met on the islands are a quirky bunch who stand apart. Many were local artists, eccentric by nature most anywhere in the world, but welcomed and indulged in Key West as just another piece of flavor and culture. Those non-artists seem to have at least an indirect connection with the island’s tourism industry, the driving economic force in Key West.

All of these nuances were missed as a child; quite frankly I simply didn’t care about the locals, not when there was promise of tightrope walkers and trained cats….

Images of Sunset at Mallory Square, Key West
Sunset street performers and artists take over Mallory Square each evening in Key West, Florida

As the sun set on my first night in Key West, I watched the performers at Mallory Square milk the crowds for laughs and tips; I soaked in the atmosphere as the cool breeze lifted strands of my hair, tickling a smile from my face at the gaped jaws of children watching the street performances with rapt attention.

Nostalgia is a fickle beast and my memory flitted back to the summers all those years ago, my undiluted joy and wonder on this very same boardwalk, and I notice that the moments etching into my memory now are the conversations with locals, the mouth-puckering tartness of a sweet key lime pie, and the mild confusion of navigating the quaint city streets.

It’s not that Key West has changed, though it has, because there is still so much of the same. I can’t go back in time and instead embraced the new version of Key West, one filled with lively pubs, snorkeling excursions and friendly faces at every step of the way.

21 thoughts on “A Little Nostalgia… A Portrait of Key West Culture, Then & Now”

    • Thank you Claire…that shot with my brothers is a favorite of mine and always makes me smile :) Thanks for stopping in and reading!

  1. We went to the keys for a few days over the summer.  We took the glass bottom boat ride out of John Pennekamp, went snorkling at several spots, and headed down to Key West for an afternoon.  It was a totally fun and relaxing time. 

    • There are some beautiful reefs over there so I imagine the snorkeling was top-notch! Relaxing is pretty much what the Keys were built for it seems and I enjoyed my time down there as well :)

    • I agree, so not a fan of resorting areas where all you do is hang out in a canopy on the falsely white and blue beaches. I loved Old Town Key West though, and the pretty wooden houses and storefronts — a lot of character there! :)

  2. I love the Keys. Me and my friends, for a few years, maybe five, went to the keys every year for my birthday. Before that, we would take trips to the Keys on the fly, as we lived in South Florida. We couldn’t go this year because I was broke and in grad school. I look forward to next year, though, and hope to get a bunch of my friends together to celebrate.

    • Oh man, I understand, the University years for me meant a lot of sacrifices on the fun end of things, but the birthday tradition is so much fun, I’ll cross my fingers that you guys can save up and make it there! :)

  3. Unfortunately, I did not get to visit Key West before it became so touristy.  But I do still love it there despite the kitsch.  So beautiful and so laid-back.

    • Oh yeah, a lot of kitsch for sure!  But still a great small town to wander through for a visit; I vastly prefer the vibe in Key West to typical beachy resort towns. :)

  4. Hey shannon, thanks for the drive! I would be a proud Floridian as well knowing that Key West is included in my state. Love the young Shannon photo as well :)

    • Aw thanks James, digging through the old pics to find it made me smile :)  I’d be flattered about the KW comment, but I mean, you have the entire Great Barrier Reef in your country, pretty awesome in its own right!

  5. Well this certainly didn’t help to end my craving to get back down there. I’ve only been there once a few years ago. That few days was not nearly enough. I don’t think I can convince her to spend winters down there on a sailboat, but I’ll keep trying ;-)

    • I completely know what you mean…a few days is just a teasing taste of the Keys, but I love your sailboat plan, I’ll have to jump on your side next time I see Maria! :)


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