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

From the Porch: Need your help: Why would anyone want to live in Key West?

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.


Wow, what a spectacular Monday morning. One of those days when I send a “wish you were here” postcard. Which got me to thinking: Why would anyone want to live in Key West?

There are a bazillion unscientific surveys that say Key West is a “top 10 this-that-and-the-other,” but those things are always about why VISITORS want to be in Key West. There’s nothing out there, at least nothing I’ve found, that explains why one would choose Key West as the place to move to be a teacher, doctor, lawyer, business owner, cop, firefighter, etc. You know, the kinds of jobs and professions that make a little-town-big-city a great place to put down long-term roots.

I used to live in a place where the first words out of anyone’s mouth when a permanent newcomer came to town were: “WHY would you want to move here? It’s awful.” Really. They did. The people who lived in that town professed to like living there, but they sure questioned the sanity of those who came with a moving van and permanent address.

Key West ought not be that kind of place. But I wonder sometimes if we’ve not gotten way far down that path over the past 20 years, at a pace that seems to be escalating. We keep asking: How can we get people to come here? How can we improve the “experience” for our visitors.

Ought we not be asking instead “what must we do to become a place where people want to live”?

Social scientists use pretty specific criteria to define a good place to live. Among them,  a livable community needs well-paying jobs, housing those jobs can pay for, good schools, access to health care, public safety, strong leadership and community participation, a sense of shared vision and goals, a welcoming diversity, things to do, opportunities to grow, a solid infrastructure and public services and a sense of community.

I believe that if Key West were to make this a great place to live, our tourists and visitors would follow along happily. But we’re so focused on making things good for visitors, investment home owners and tourists that we’ve lost sight of the locals.

So, this is where I need your help. Whether you already live here or think you’d love to live here, what criteria must be solidly in place for you to stay or come with a moving van?



  1. Natasha

    I have loved the Keys since I first visited in 1999 as a 24 year old who felt like I had landed in paradise, sitting at a bar in Geiger Key and nursing a virgin Pina Colada. I then daydreamed extensively until 2011 about the chances of living there. Now, as an accountant, having moved from the UK to Canada, and with two girls – one and teen and one a “tween”, I see a reality that makes it even hard to visit. The last time we were in Key West was in 2005, straight after a hurricane, for fantasy fest. My youngest was 18 months and it was “safe enough” to be there with an under 18 year old. Since then when staying on Summerland Key we ventured in with two children and a couple of seniors.
    I had to try my hardest to ensure no one looked in the windows at the t-shirt shops on Duval as the wording on the window display products was not for anyone under 18 or seemingly anyone over 65. I dont recall it being that way when I was there before.
    I wonder if it was always so crass. I have brought my two girls up to support any and all love. I dont care if you are straight, gay, bi, whatever… but have some decorum, some class on the main street with what you sell. I dont want to take my family to a porn shop….
    So now…. I am back to wondering how people live there with kids, let alone how they afford to and also, do I want to pay a stunningly high per night amount to stay in a place thats so very beautiful but so very seemingly full of stores that I have to try to stop my 11 year old from looking at.

    • LGC KWIN

      Oh, Natasha, what a beautifully written column. You’ve captured the dichotomy of today’s Key West. That beauty, magic and mystique cheeck-by-jowl with what should be called the “lack of class.” Locals stay away from Duval. That’s pretty much the only way to live here and not weep every day. But… There’s a new city commission and a new mayor. For now, we are hopeful.

  2. Charles L

    Thank you for raising this very question. The wife and I very seriously looked at moving to the Keys two years ago, long before Irma and it didn’t look pretty then. From what I can see, it has only gotten worse.

    We love the life style there and enjoy our time there and can’t wait to be back there again next year. We both are professionals in the media, myself in the technical end and my wife in content. But we are getting on the back side of our working life. so unless you are in your 20’s or 30’s and can afford to live on the wage of a bartender or wait staff or tee shirt seller or taxi driver or boat hand or beer truck delivery guy, Key West or the Keys in general is a pretty awful place to live, financially speaking, unless you are retired with a LARGE bank account or independently wealthy or have lived there for 20 plus years before the prices got out of hand or a native.

    While I am not a poor man, the Keys are too rich for me to live there. It would take selling everything I own, including property I own along the coast of an Atlantic southern state to just be able to buy a 2 bed 2 bath small condo in Key West with no way to really stay any length of time after that. And from what I can see from a distance, forget a rental. They don’t exist anymore, at a reasonable price. And if they did, what kind of a job would there be to support us? Last time we were there, I asked a taxi driver what he had to do stay in the Keys. He said without missing a beat, multiple jobs. Doesn’t sound like paradise to me.

    I admit my heart is in the Keys since my first visit there but I live somewhere else where I can afford the cost of living. Thanks to the Internet, I follow a lot of the media outlets there (obvious I guess since I am replying to this post) and even frequently listen to the radio stations there via streaming (I enjoy the news on US1 Radio) and watch the news on the TV stations from Miami via streaming. I do try and keep up what is happening in Monroe Country if I can’t be there. Closest thing I may ever get to living there.

    Florida Keys. Great vacation destination. Florida Keys. A permanent home? Fuhgitabutit.

    So our dream of living in the Keys will more than likely just remain an unrealized dream. Until I win the Power Ball.

    • LGC KWIN

      Thank you, Charles, for taking the time to share comprehensive and important comments. I know you are not alone. I’m intending to write a series on the subject — and, hopefully, help shape some discussion here. I know this for certain: Had my husband and I not made the move in 2008, we could not do so today. Priced out of the market in less than a decade.

Related Posts

Pin It on Pinterest