Why People Visit the Florida Keys, and Never Leave

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During my week of traveling the Florida Keys from Key West right up to Miami, I met a lot of people, almost all of whom are supplanted from somewhere else, but who now call the Keys home. Here are their stories, which explain the multi-faceted magnetic appeal of the Florida Keys & Key West.

This post was originally published in 2014. It has since been updated for accuracy of links and content. 

The Key West Community

Key West Florida sign; the southernmost of all the Florida Keys

Key West in particular has its own unique flavour; it’s the only place in the Florida Keys that you can reasonably live (or travel around) without a car, which in turn attracts a more bohemian crowd from a variety of financial and social backgrounds – all of whom live in symbiotic harmony with both each other, and with the throngs of tourists.

Unlike most other tourist towns I’ve visited, Key West locals (most of whom are from somewhere else anyway) embrace tourists. Tourism not only represents their income, but also their entertainment; thus you would be hard-pressed to find a “locals only” establishment, nor can you find any of the dissension towards tourists that is usually prevalent.

Said one friend, “Key West is a live and let live kind of town”.

Key West is also referred to as the Conch Republic (with people born in Key West referred to as “conchs”), and was actually a republic – it’s own country – for one whole day in 1982. Although it’s only two by four square miles in size, I’m a wee bit disappointed that they couldn’t keep their independence; it truly is a unique and special place that deserves special recognition.


Carol and Zero: Visited and Never Left

Carol’s story is more the norm than the exception. She visited from Minnesota over 30 years ago and never left. When asked why she loves Key West, she came up with a sentence full of complementary and contradictory terms, including “warm, funky, palm-tree-hippy-ramshackle, Cuban community”.

And that was all off the top of her head said with rapid fire enthusiasm. If given more time to come up with an answer, I’m sure she’d have included yet more adjectives.

Zero with his bicycle taxi, in the Floria Keys

Zero, a guy I used to live and work with in Hawaii (and was thrilled to catch up with in Key West), was a wealth of information when we met up for a quick tour on his Bike Pedicab. He spoke of the “salty pirate feel”, discussed how easy it is to make money (for those who have even a moderately enterprising spirit and can control their partying), and described the “frontier feel” Key West has due to being (quite literally) at the end of the road.

And despite the harmonious relationship with tourists, Zero said he can always spot the locals; largely because Key West has a small town community feeling so familiar faces quickly become friends.

I absolutely loved Key West, and would return in a heartbeat. From the daily “sunset celebrations” in Mallory square complete with street performers and vendors, to the surprising amount of history, unique architecture, colourful vibe and Caribbean feel, it could even be a place I’d try calling “home”.

selling coconuts in Key West at the Sunset Celebration

Traveling up the Florida Keys

After a few days in Key West, I traveled up the chain of Florida Keys and met more people with similar passion-infused stories, each settling in the Keys for different reasons.

Sarah and Rick: Nature

Nora Dunn, The Professional Hobo, kayaking in the Florida Keys
Photo courtesy of Seattle’s Travels www.seattlestravels.com

While going for a sunset Kayak ride on Big Pine Key, one of the guides, Sarah from Vermont, couldn’t contain her enthusiasm for her relatively new life established in the Keys. She spoke of being surrounded by eco-minded people who all enjoy the ocean and nature in their own way.

Rick, an ethnobotanist from Connecticut, oozed passion for all things growing while leading a (surprisingly) enjoyable and informative tour of the Botanic Gardens at Kona Kai Resort. He studied and lived in many places (including a few places in Peru), and settled on the Florida Keys for its incredible lushness.

Captain Steve and 1st Mate Mitch: On the Water

deep sea fishing reel and lures in the Florida Keys

One of the main allures of the Florida Keys centres around fishing and boating (which stands to reason). While sport fishing, Captain Steve told me how he grew up on an Arkansas farm and lived and worked all over the US, but decided to “retire” to the Florida Keys to run fishing charters aboard his boat The Warrior. Although I chuckled at this hard-working “retirement” lifestyle of his, I also understood; for him this is a labour of love that has helped him reengage his life in a new way, borne of pleasure rather than necessity. His story was far from the only one along these lines.

Mitch, a 15-year old first mate on a deep sea fishing charter in the Florida Keys

Steve’s first mate for the day was Mitch, a 15 year old who seems as at home in the Keys as any native conch. He moved with his family from Chicago five years ago, after his father had a heart attack and they had to get away from the cold and stress of the north. “The weather, obviously!” was his response when I asked him what he loves most about life in the Florida Keys. (I’m pretty sure he also likes the fishing, given his obvious talents and job as the youngest first mate I’ve ever met).

The Multi-Talented Bret

silhouette of bartender with a palm tree in the Florida Keys
Photo courtesy of Seattle’s Travels www.seattlestravels.com

Aside from mixing epic drinks at Sundowners in Key Largo, Bret is studying to become a firefighter, has helped a friend set up a business, and I suspect he has a few other irons in the fire as well. Like Zero, Bret spoke of how easy it is to make money in the Keys, and said he loves the community feeling. “It’s the island life; everybody knows everybody”.

Ashley: Underwater Life

children's drawing about coral
Coral Restoration foundation tabs hanging on coral in an aquarium in the Florida Keys

Ashley is from Colorado, and came to the Florida Keys after studying Marine Biology. She works at the Coral Restoration Foundation, which is restoring what is the third largest coral reef in the world – right off the coast of the Keys. She and the other employees, volunteers, and interns at the foundation have an obvious love of ocean life, and are doing their best to preserve and restore it to its former glory.

Thank You Florida Keys – and Inhabitants

Beach and fishing gear with blue sky and palm tree

Between the “island life” community feeling, the great weather, lush nature, marine and boating life, bohemian feel, and Caribbean flare, a mere week was all I needed to be sold. I’ve visited a lot of places in Florida (like Hollywood, Santa Rosa, and 30A), but it was the Florida Keys (specifically Key West) that kept a little piece of my heart.

Thank you to Florida Keys & Key West for hosting my Florida Keys trip.

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24 thoughts on “Why People Visit the Florida Keys, and Never Leave”

    • Anna – Different strokes for different folks! Even just to Visit, I believe you’d love it. 🙂

  1. Hey Nora! It warms my heart when people come to Key West and discover its magic. It’s not unusual for first-time visitors to the Keys to appreciate the weather and the laid-back vibe. But when you take the time to talk to the locals–transplanted or home-grown–you start to understand the enchantment of this tiny string of islands. For a world-traveler like yourself to be captivated by its charms is telling! it’s different here. Some people vow to visit annually. Others get caught in the allure and stay a year or two. But for some of us, the magnetism holds us here longer than even we imagined. I came to Key West on vacation a few times to visit friends who’d decided to stay a while. One such two-week vacation turned into a 3-month stint, and I knew I was hooked. I went home, packed up what I thought I couldn’t part with, planning to settle in for a year or two and then continue travelling. That was 1992. Two decades have flown by, and I’m happy to say I’m stuck in paradise! Next time you’re in town, (and I know you’ll be back!) be sure to stop by the bookstore and say hello. I’d love to take you snorkeling on some of our favorite patch reefs, maybe even spearfish for dinner! Until then, I’ll travel the globe vicariously through you.

    • Hey Suz – Awesome story! “Stuck in paradise”…..what a great problem to have!
      You’re right: I’ll be back, and when I do come back, we’ll connect for sure. Thanks for everything, Suz!

    • Zoe – I didn’t get any chance to dive, but I’m under the impression that the diving, especially around Key Largo, is pretty epic. And you can volunteer with the Coral Restoration Foundation – something I would totally do if I had more time there.

  2. I don’t want to sound like a scold, or a buzz-kill, but I think you’ve only hit the highlights. Allow me a story, if you will:
    My husband and I went to Key West for our honeymoon in 1995. Like you, and so many others, we fell in love with the island. Enough that a few years later we decided to try to buy a house. Not to move to yet, but to rent out and have for “later”. That was quite educational. We met many, many young people living in very crowded homes; people had turned nearly every room they could into a “bedroom”. Alot of the people we spoke to were holding down 3 crappy part time jobs to live there. At the same time that we were trying to buy, the city council declared that no more houses could be made into short-term rentals. So every house that already was suddenly tripled in price. (We were unable to buy.) Its a beautiful place, but as Jimmy Buffet says “remember Paradise doesn’t come without a price/let me make that abundantly clear”.

    • Hi Natalie,
      GREAT observations! Indeed, I asked a friend what it was like to rent there, and he said a 1-bedroom efficiency runs about $1,100/month (if you’re lucky) – on par with some of the mega cities of the US! Ouch.
      And you’ve also discovered that, real estate prices are almost consistently very high in a place where real estate is intrinsically limited (ie: an island).
      Sorry you were priced out of the market…Jimmy Buffet knew something when he said Paradise has a price!

  3. What a sick life these people lead … just like my life in the mountains over the past few years, only with palm trees! 🙂

    • Hi Katie,
      Indeed! I can’t decide if I like the mountain life or the ocean life better….I have an affinity for both….

      • great story nora, while part of me wants to believe this amazing tribute to a very underrated part of America, the cynic in me knows better, I cant help but see your story as nothing more than a dog whistle to attract more white people to the area and push out Hispanics, let me explain ,I’m a third generation Mexican/American from San Diego California, I’m 35 yrs old and spent many years as a environmental analyst in the state of Texas, I have lived and worked in many places all over America, NY, Wisconsin ,Washington state, florida etc. the one thing i noticed is that Mexicans and other Hispanics are not respected like we are in California, being a southern California native I must say has sheltered me from the ugly face of bigotry still alive in much of the south and ESPECIALLY FLORIDA. never have i seen such vitriol and animosity toward Latinos like i experienced in Florida, from stares , to bad service, to rude comments in 30 yrs of living in southern California i never once experienced those things, here is my take on the florida keys and key west, its a place where white people mainly from the eastern and mid western states go to retire, these whites are not like the nice Irish whites in California or the openly tolerant Italians in NY and NJ, these whites are of german decent from places like Chicago, st Lewis, Indiana and Wisconsin and Minnesota , german americans are truly the same bigots who burned jews alive , i can tell a german american by their small slanted asian eyes wide cheek bones and that red sunburned skin complexion .

        i will never spend another dime in florida, for what? I’m blessed to have been born and raised in san diego ca, and i have all the pacific west coast at my finger tips, southern california in my humble opinion is better than miami always has been always will be, our oceans are better, our scenery with mountains and deserts is better and our sunsets are second to none,

        florida is an over hyped swamp land

        thanks but no thanks.

        • Hi Ralph,
          Thank you for weighing in with your experience and opinions. Although I’ve certainly found certain parts of Florida to be incredibly homogeneous and often racist, I didn’t feel it as much in South Florida, where there is a much bigger hispanic and multi-cultural population than in other parts.

          • miami dade county is the sole exception, miami, south beach are huge tourist attractions no question. but try driving down the coast from Jacksonville ,st Augustine ,palm coast and Daytona, if you are lucky enough to make teh drive down south without an incident consider it a miracle, I wont even mention the florida/Georgia line or the pan handle . the west coast is truly another nation in itself, it is a hispanic haven a true bubble that doesn’t have the real american experience , I guess its safe to say california is now mexico, but even texas which has a large mexican/american population still has plenty of bigots.

            I ve done plenty of research about this topic, leaving california was a real culture shock and a wake up call to me , I have found that the most racist places in america have a large german american presence, in st louis the majority of people are of german decent while in New jersey the majority of people are italian americans, while jersey people can be rude its nothing like the hate in places like south carolina, florida, georgia etc.. washington state has a high rate of hate crimes and as expected is also a very high german american population.

            north carolina is racist also, but this state has mostly scots irish, and english descendants,

            the irish in boston are rude but in general good people. thier is so much to learn about the history of racism . but the most dangerous people are german americans and luck have it they are also the largest ethnic group in america at over 55 million, mexican americans are at 30 million just to compare.

            i think its a sad reality that when researching travel information, racism has to be a important consideration of the place i’m visiting

            oh well such is life in 2015

  4. I am weighing in a “little late” on the conversation. I apologize for that however, i am also of Hispanic heritage and have been to Florida more times than I can count. As far as racism “well” it’s unfortunately everywhere. I also attended Chico state and lived in 4 different cities in California including riverside. I personally experienced racism but… that wad because Latinos that I was a “white man”. So ….. morale of the story if you don’t love the US? Leave … with your attitude I don’t think any one will miss you. Adios mi amigo!!!!

    • Hey Ben,
      Thanks for weighing in! And you’re right – unfortunately racism exists everywhere, to different degrees.

  5. P.S. key west is a great place to visit unfortunately it’s high cost of living kills many dreams of becoming a conch.

    • Hey Ben,
      Yeah, as much as I’d like to check out Key West more as a place to hang my hat for a while, I gathered it might cost a pretty penny.

  6. I first became aware of KW watching a BBC documentary on PBS here in Los Angeles in 1994. That started something of an infatuation that I had with Key West that lasted for well over a decade. I finally managed to visit in 2005. It has a certain uniqueness about it, and I can see why it drew many artists and creative types in times gone by, much like NYC did in the 1950s-1970s. But like NYC and Los Angeles, gentrification has created an environment that no artist can afford to live in unless they’re from a rich family / trust-fund baby. Key West is worse off since it has no job market to speak of outside of retail / tourist stuff. It really doesn’t matter how many college degrees / skills you have in Key West; you’ll be trying to get the same part-time low wage job as the high school grad.

    In 2019, Key West is a place to bring money to, not to make money. In other words, come for a visit, but think twice about moving there.

    • You’re not wrong about this; to make money in Key West you need certain skill sets that are applicable to the area and its micro-economy.
      Perhaps it’s why the people who have found a way to make life work in the Florida Keys in general, love it so much.

  7. I was born and raised in Key West, and so was my father and grandfather. It is one of the most beautiful and magical places on the earth and definitely in the country. Sure, there are tourists and some negative things, but overall it’s still one the most amazing places on earth. The bike rides, the sunsets, the islands, the ocean and of course the people. I have no idea what all the racism talk is about. Key West accepts ALL. If you have ever been you know this. Sure, it’s changed over the years and it’s lost of the old school funky vibe but it still has magic. I promise you that. Unfortunately, money, greed and tourists will eventually erase everything. ENJOY IT WHILE YOU CAN!

    • Thanks, Cuzzy! I certainly enjoyed my time in Key West, not so long ago. I saw a very open social scene. Then again I was only passing through. So it’s great to hear it from a long-time local!

  8. On your statements, ‘Cuzzy Moto’:
    1) ‘sure, there are tourists and some negative things’, and
    2) tourists will destroy everything

    Your neighbors who work at CVS, the waiters, the bartenders were collectively rude to the extent on this trip that I won’t come back again. I’ve been here 5 times, I’ll not do the 6th. I come here for the gay resort, not to bother anyone or anything.

    Goods were falling out of my hands at the drug store, where I asked where the baskets were. She actually performed a hostile dance in front of me after speaking 500 words of English, claiming she did not understand, to brush me off. 80-100 additional words of English to me after.

    I absolutely feel the negative presence we tourists bring. Never again to your town.

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