The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

Key West winter week

The real Key West | What’s behind those dreamy tropical photos

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


There’s nothing like a shared Instagram pix or a Facebook album to entice visitors to Key West. All that sand, sunny blue skies and big puffy clouds as background for sitting in a kayak in the green, towering mangroves puts our tiny island on a lot of folks’ bucket lists.

Heck, even I am seduced.

I’ve said for years that one of the joys of living in Key West is that I live in that rare place others dream of visiting. When the Conch Train used to snake past my house half a dozen times a day, I’d stand out front, wave and wish them happy vacationing. They’d laugh and not a few would shout back “You’re so lucky to live here.” I’d nod and wonder if they could smell the summer’s unwrapped fish remains rotting next to the spoiled milk in the green trash can.

The Conch Train’s leisurely roll down my block ended a few years ago, replaced by e-bikes going the wrong way with loud riders narrating their GoPro videos and barely looking up from the screens to see the neighborhood. They’ll go back to their vacation rental or hotel, edit that video to remove trash cans, cars, utility lines and such, leaving a slick, TikTok-ready post that’s as misleading as it is lovely.

Real Key West

Real Key West | Destination tourism

That’s the way of destination tourism. Always has been. I remember visiting the Dominican Republic decades ago, lured there by marketing pamphlets that showed me the spectacular resort and its endless, empty, jewel-toned water and beaches. They didn’t share the equally endless miles of dirt-poor, subsistence-level shacks that lined the barely passable roads that ended in a gated resort. My naivete shames me.

Key West has pretty much always been a siren call for tourists. But over the past three decades, we’ve inexorably moved away from being a working town that welcomed visitors to a bucket-list visitor destination that’s undermining the working town that supports those visitors.

The pace of that shift escalated in 2020, when Key West was among the very few tropical destinations open for those champing at the bit for an escape from Covid-19 lockdowns. They came by the tens of thousands, demanding, entitled and determined to push the limits of both commonsense and politeness among strangers. Their richer developer cousins bought up housing stock and turned former homes and residential rentals into vacation rentals and second (or third) homes.

They didn’t come back this summer of 2023. There has been both a sigh of relief and a shared anxiety attack over diminished revenue streams to pay the bills. Home prices, which still tickle the underside of obscene, have dipped, though they’ll likely never be affordable except to the folks who pay cash for a $3 million house.

But, I digress. Back to my point: It annoys me to no end when I hear visitors complain about our awful beaches; or having to make reservations months in advance; or stand in line for a hour to get into the Hemingway Home; or fight for a free parking space only to find out it’s marked “residential” and park anyway; or whine over how expensive things are and how it’s not like that where they came from.

Are they as naive as I was over the Dominican Republic? Probably. Surely they did some homework before booking a Key West vacation? Probably not.

So they get here and are shocked, shocked, I tell you, that there’s trash in the streets and mold growing down the walls of their expensive rental. That it’s hotter than Hades with a steam bath thrown in. That they’re not going to walk up and buy a ticket to the Dry Tortugas since the ferry is booked months in advance. That getting to Smathers Beach means navigating a construction zone. That Uber drivers are often from Miami and have no clue how to get around town. And, that locals, even their so-called favorite bartenders, aren’t 100 percent grateful for the two buck tip.

If I’m having a good day, I’ll still wave at the Conch Train folks and wish them a happy vacation. They no longer see me or fancy that they, too, might live here — because they’re in the smartphone hunch on the hunt for their next post.


  1. Laura Roake

    I have spent my entire life in Tampa. Been to the Keys many times (last time in May) and still enjoyed going there. But things are moving at such a rapid pace these days, everything is getting overcrowded, prices are so high, it really isn’t just Key West. This article hits the nail on the head for so many places in Florida. It’s like they say, you can never go home. Problem is, some of us never really left home, it just feels like we have at times.

  2. Lynda Schuh

    Pretty interesting there Linda…You nailed it in so many places…
    and it hurts….
    I was there last week for Little Toni Tarricinos memorial and to visit with Capt. Finbar (in Miami Beach) and a few other friends from my ‘working on the water’ days and my timing coincided with a fundraiser for Capt. Finbar at the Schooner. It was an awesome reminder that some wonderful folk are still living and loving it there (despite the ‘crap’ that has entered our little island)….but I have to note that either those present have owned a house for many years or are in senior housing or public housing.
    However it was still a magical key west evening with comfortable faces and voices and laughter and shared memories, and a good outcome for Finbar…Both he and Capt. Tony had a lot to contribute to the soul of Key west during my time there.
    I don’t blame individuals making a living but the real estate industry has ruled the islands for many years now and it has no conscience…even outsiders, with the support of local agents, buying up houses just to rent on vrbo or airbnb…I say shame.
    There is so little local stewardship…..there is some, and people still care, but it is hard to watch, sometimes hard to be there….despite the fact it is happening everywhere in Florida….and as a 50 year resident, I hate it and can’t imagine what those before me felt or the conchs when we all started swimming in, me right after Mariel boat lift.
    I’m in Silver City New Mexico now 4 years and yes it is the land of enchantment and can be as exotic as the islands once were and there is sooo much open land and mountains and few but very interesting earthy folk including many old cowboys, but it is still not Key West…and never will be….
    thank you Linda…looking forward to reading more….
    Lynda Schuh

    • Linda Grist Cunningham

      Thank for the note, Lynda. Spot on in so many ways. I appreciate your taking the time to share.

  3. Heather Dampf

    Key West is where my heart lives even if my address is in Wisconsin. When people ask me what it is I love about KW, it’s hard to explain it to someone that has never been. It’s a feeling of being home. Where it truly is ‘one human family’.

    • Linda Grist Cunningham

      Heather, that’s exactly how I feel. 🙂

  4. Cindi Wheeler

    I moved down in the early 80s; 19 years old from a small Alabama town. Fell in love with the slower pace, the friends I made, the beauty, even the tourists were usually pretty cool . . . even found someone special. Then came cruise ships; rude tourists who screamed “I could have gotten this cheaper in Mexico” and wanted to know where to get drugs because apparently we were all stoners. Time marched on, three years later we moved to Virginia to help his older parents. Went back a few times, lives changed and we divorced. We got back together 4 years ago and have gone back several times. I still love the island, but it really isn’t the same. Franchises used to be only in New Town, now there’s a Walgreens and Wendy’s and others on Duval, everyone is either trying to show how drunk they can get or how much they can get done in three days without ever stopping to see the magic, the beauty, the enchantment . . . We’ll be back down in October (even Fantasy Fest has changed from it’s early days, but it’s still the best people watching!), but we won’t be the ones rushing around – we’re the ones slowly walking through our old stomping grounds and wondering whatever happened to so and so and taking the time to smell the flowers!

    • Linda Grist Cunningham

      Oh! You say it so well!

  5. Rick Ellison

    We first visited Key West in the 70s. We were regular visitors until 2010. I still like it but it has become overly expensive and somewhat rowdy. It has been awhile since we’ve been there maybe I should give it another chance.

    • Linda Grist Cunningham

      That rowdy and expensive has increased, and I do oft complain too much, but I can still find the magic.

  6. Donna Wallen

    Yes, there is definitely two very different sides to Key West and the Lower Florida Keys. I’ve seen it from both sides, first as a tourist and then as a 5-yr resident. Loved it from both perspectives even with all its flaws (which are mostly caused by rude tourists and greedy politicians. Haven’t been back since 2017 and know a lot has changed, esp. to Stock Island but hope the waters are still that perfect shade of aquamarine; and the islands are still lush with Poinciana and Palm trees, Bougainvillea, Hibiscus, a Gumbo Limbo or two and that street artists and performers still dot Duval Street as when I left.

    • Linda Grist Cunningham

      As much as things have changed, the island remains a magical place. Sometimes I have to look a little harder, but I can still find that joy.

  7. Tonja Weddle

    I visited in early 2023 for the first time and fell in love. I’ve never felt such a draw to a place before. It was love at first sight. I can’t wait to come back.

  8. Bill & Antonio

    My husband and I have been annual visitors to the island since 2007. We even had our wedding on Smather’s beach. We love the “real” island and always stay in Old Town at Alexander’s Guesthouse. You are correct about the change in who visits the island now. We usually avoid Duval as that’s seems to be where you will find most of the “entitled-minded” crowd. Nevertheless, it’s still our favorite tropical spot to spend a week and kick back and we look forward to our next visit later this year.

  9. Jammie McCormick

    I saw a total eclipse at Virginia Beach in 1969. An awesome and spiritual experience. We camped on the beach. Next morning, someone said ‘let’s keep driving’ and we ended up in Key West. It was paradise to me, and always will be. I visit once or twice a year, try to ignore the changes, and visit my favorite spots. My husband and I would always look for employment opportunities, with no success… we’re never giving up.

  10. Carol Ingles

    I totally Agree with the comment related to “where it’s real”. I keep saying that the Keys are fighting to keep what was the “real Florida” of decades ago. Love sitting
    in a kayak on a reef as I truly believe in the total healing impact it has on me. Stay who you are Keys❤️💯

  11. Cheryl Jarrett

    I had never heard of key west. When my last son left home I decided to move to a better place. Job applications led me to KW. Everybody told me to jump on it. I fell in love with the beauty, the laid back feeling of most of the locals and the genuine beautiful hearts of the people. Been home for over 20yrs now. I thank God I found it. Love our island!

  12. Natasha

    I first came to Key West in 1999 and have been blessed to be able to return many (although not enough) times since. I love every part of it, especially where it’s real.
    I hope to come back soon. It’s paradise to me

    • Linda Grist Cunningham

      So true, Natasha. Come home soon!

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