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

Leave Key West

Is it time to leave Key West? 5 ways to (sorta) know

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.


Twice in the past week someone asked me if it’s time to leave Key West.

That’s not a wholly unusual question. Folks leave Key West for careers on the mainland, for school, for family opportunities, for affordable cost of living, for health care, for plain old variety. In that sense, we’re no different from everywhere I’ve lived; sometimes one just knows and goes.

What sets the current “time to leave Key West” questions apart is the underlying, weary dissonance that has become the drumbeat of our lives. We have lost our sense of proportion. The slightest disagreement among friendly acquaintances triggers outrage.

I’m weary, too.

The Florida Legislature spent the spring doing end runs around home rule and ensuring Florida’s not a great place to live unless one (a) looks like the folks who run the legislature; or, (b) keeps one’s head in the sand. The friends of Gov. Ron DeSantis aka Pier B want to expand their Key West cruise ship docking facilities, flouting the collective will of most Key West voters.

My wind and flood insurance costs are about to match my mortgage. Friends are testing positive for Covid-19. I’m so tired of folks whining about cutting down subterranean termite-ridden, darn-near-dead poinciana trees that I’m inclined to take a chain saw out myself.

That’s the short list. We don’t recognize our island, our state or our country. None of us, so don’t be thinking this is only about politics. That ephemeral sense of control we imagined we had over our lives has ghosted us. We do that primitive fight or flight thing and we ask if it’s time to leave Key West.

Leave Key West

Is it time to leave Key West? Five questions to ask

So, what do I tell folks when they ask? The same five things I tell myself.

It’s time to leave Key West, if:

  1. It’s time to leave Key West if any of those six things I mentioned up top apply. Need health care? Go. Headed off to school? Go. Need affordability? Go. You get the point. Eventually that health care thing is going to catch up with Ranger Ed and me and we’ll head for the Shenandoah Valley to a continuing-care retirement center that my dad called the “cradle to grave.”
  2. It’s time to leave Key West if you have a better place in mind. I know some folks can describe how much they would enjoy living in, say, Asheville or Chicago. I can’t wrap my head around that. I’d happily die on my porch looking at the mango tree as its roots punch holes in my pool. So, yeah, that one won’t work for me. There’s nowhere else I want to live. Not even the Shenandoah Valley.
  3. It’s time to leave Key West if you think you’ll be politically comfortable in, say, Texas or New Hampshire. Heck, one of the reasons Ranger Ed and I moved to Key West is because we liked the libertarian culture of “you do you; I’ll do me.” There’s no predicting how the next decade of cultural and political shifts are going to change all 50 states. One could be trading Frick for Frack. Florida’s already down one rabbit hole and I’m darn sure we’d not have predicted that, after those hanging chads. I’ll hold my nose and stay here. I think. For now.
  4. It’s time to leave Key West if you too frequently open conversations with “I remember when” followed by a deep, old people’s sigh. I am of the generation whose early-adult mantra was “don’t trust anyone over 30.” Now that I am (significantly) over 30, I’m inclined to keep thinking that. Why? Because lamenting the loss of the old days is what old people do. Key West is in the middle of a transition unlike any since the Navy pulled up stakes in the 1970s or the Depression darn near wiped us off the map. We reinvented our island then. We will do so again.
  5. It’s time to leave Key West if you’ve forgotten what it is to love Key West. I’ve told countless Key West newcomers that if they love the island, warts and all, the island will love them back. We live in the place others but dream of. We live in the place where they can escape momentarily today’s dissonance.

Is it time to leave Key West? You do you. I’m staying.


  1. ed cabaniss

    Yep, good for you.
    The same seems to apply to me here at Holden Beach.
    Keep it together.

    • Linda Grist Cunningham

      Which is why it rarely makes sense to up and move just because one’s got one’s nose out of joint. Where else might one find things different? Pretty much no where I can think of. 🙂

      • Pam Flowers

        Thanks, Linda. Andrew and I are! 100%

        • Linda Grist Cunningham

          Great news, indeed!

    • Mimi burke

      Wish I could live there

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