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

Zach rocks

Unseen in Key West | The neighborhoods tourists miss when they visit

Unseen in Key West | The neighborhoods tourists miss when they visit

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.


05/10/2025

Y’all know I love listening to the folks who bike or walk past my porch. Snatches of conversations float on the breezes, partial observations that when taken together weave a passable research study on what visitors think about our island. Mostly these are happy campers, delighted to be here and wishing they could stay longer.

Sometimes they’re flat-out lost. Striding purposefully toward the Eisenhower-Truman intersection at Bayview Park when they thought they were headed to Duval. Bickering about who made the mistake of turning the wrong way on the one way street. Stopping smack in the middle of the road to read that dog-eared map or to peer bleary-eyed into a smartphone screen in the sun’s glare. I’ll walk out to the gate to help when I can.

Most times, though, they’re simply passing by, heads on gimbals turning every which way to admire the houses, exclaim over the orchids in the trees or the poincianas pridefully tossing their red-headed glory. Like the young biking couple Tuesday morning who delightedly remarked to each other, “Oh, my, we’re getting to see things other tourists don’t.”

I forget sometimes that our visitors, especially first-timers and short-stayers, don’t see much of Key West. Tiny though the island is, visitors can be forgiven if they think Key West is the sea-to-sea stretch of Duval Crawl bars, CBD stores and assorted shops, t-shirt vendors and eateries. They might, if they’re up for more walking, throw in a handful of nearby cross streets. If they’re doing water sports and sunset sails, they get a superficial sip of blue water.

They love all that, of course, but my happy couple’s comment Tuesday got me thinking. What do our visitors miss when they’re tethered to the asphalt in Old Town’s commercial district?

Key West neighborhoods

Key West neighborhoods | A lovely place to live

The neighborhoods top the list. Even with the unrelenting gentrification that has co-opted our residential neighborhoods and turned them into vacation rental and second-home hubs, Key West’s distinct neighborhoods retain at least some of their original personalities.

As long as you get half a dozen blocks sideways from Duval toward the cemetery, Old Town retains much of its historic architecture and 1800s appeal. And it’s so darn pretty these days, what with renovations, crisp white paint and cleaned and sorted landscaping. Oh, I know, I know, some of you lament the passing of ramshackle, but let’s be honest. Old Town was always a rich people’s neighborhood with sprawling homes and manicured lots. Old Town today looks more like it did when it was new.

The Casa Marina District boasts those mid-century modern concrete, steel and glass homes that made South Florida famous. Sure there are eyebrows, Old Florida porches and cigarmaker cottages tucked here and there, but the Casa is Key West’s interpretation of South Florida’s 1950s boom.

Bahama Village retains, despite its own gentrification in the past decade, its cheek-to-cheek mix of high-priced homes with old Conch, under-permitted construction and public housing. Bahama Village is that eclectic, serendipitous neighborhood that defines mixed use in Key West and the neighborhood that most closely still resembles old Key West.

The Meadows, just east of Old town, has always been a locals neighborhood and still is home (mostly) to permanent residents. It is a crazy quilt of historic architecture, 1960s and ’70s mid-century concrete block, new builds that blend in, Conch cottages and public housing. If you were to play a game of “which of these are different from the others,” you’d lose your mind in the Meadows because they’re all different. White picket fences and lots of green growing things tie the neighborhood together.

South of Truman, which kinda-sorta encompasses Midtown and parts of Old Town, languished for years behind the renovation frenzy that rippled through other island neighborhoods. The pace picked up in the past decade, especially since Covid, turning dozens of, shall we say, challenged structures into spiffed-up show places that often are second homes and vacation rentals.

Key West, warts and all, is a stunningly lovely place. It’s easy in my daily hustles to stop seeing the island and, instead, to swear at the traffic as I dodge the growing pothole on Eisenhower or roll my eyes at gawking, awkward tourists and the locals who run stop signs in a mad dash to get somewhere two minutes quicker.

I need to remember my biking couple, who with wonder in their voices, said, “We get to see things others don’t.”

15 Comments

  1. Charles Layno

    Our last visit in 2023 was not so much the tourist traps that we had done in past visits, but more wandering around like a local might. Taking the walking foodie tour, boat trip to Sunset Key. Going to the Salvation Army Store on Flagler. Walking a lot of the paths Jimmy Buffet might have in his Waddle Ave days. Not so much the bars but actively looking for the places the locals might go to get the real vibe of the place. Places many tourist don’t see or go. It was heaven. Some might say it was a waste of all that money to go to Key West and not do any of the “Key West things”, but we think we did more “Key West things” in that one week of wandering than we did in all the visits so far. We didn’t make it to the Cemetery, but we figured we needed something to look forward to the next time we visit, hopefully in 2026, after retirement when we have time to really enjoy “paradise”. Hopefully the prices will be better then too. But we are not holding our breaths on that one!

    • Linda Grist Cunningham

      Perfect!

  2. Margo

    You left out new town , the red headed step child of Key West, all the way out there as those in old town say. Smurf village, Riviera drive, Eagle and Duck with their bigger yards and gorgeous blooming trees. The sides streets off Northside drive and all the numbered streets are lovely to bike through. The Staples bridge keeps you off Flagler too.If you ignore the Taj Ma Awful going up in the 3400 block of Eagle that is being built in place of two cottages and 2 poincianas that used to reach across the street to another poinciana (our own canopy road) it’s lovely in New town.

    • Linda Grist Cunningham

      You are absolutely spot on. I ran out of space before I could include New Town. Thanks for capturing it so well!

  3. Brenda

    Good reading right there Mrs. C!

    • Linda Grist Cunningham

      Thank you, Miss B!

  4. Cecile Freemond-Brown

    Love this description and love our neighborhood. I am relatively new to Key West…. One year, but when I talk to people at Fort Zach in my daily duties, I have people tell me that I’m a great ambassador for the island. I’m also grateful that you and ranger Ed are my neighbors.

    • Linda Grist Cunningham

      Awwww, and back at ya!

  5. Sharon wells

    Lovely descriptions of the historic and some non-historic ‘hoods. Well done, Linda. It’s a special spot that’s for sure.
    I’m wiring on editing and reviewing my Walking and Biking Guide to key West. For amazon Publishing. Do you think there’s a market? Interested in your thoughts. Thx

    • Linda Grist Cunningham

      Thank you, Sharon. Since you are THE expert on Key West architecture and homes, I am humbled. And yes! There’s a market for your updated guide!

      • Sharon wells

        Thank you!! David Sloan is advising me on the Amazon Process.
        I’m still researching individual homes for owners, in case anyone inquired!

        Maybe you and Ranger Ed will Vidit Merida at some point. I love it here.

  6. Clark Luster

    One of my jobs in Old Town is helping tourists stranded at the corner of South and Alberta poking at their phones. I always ask ” Can I help you?” And 99 times out of 100 they say yes. They are walking toward The Casa Marina but want to get to the Butterfly Museum. I’m old but I can remember being in their shoes.

    • Linda Grist Cunningham

      Good for you! You’ve probably saved dozens of folks from a family squabble once they realized they weren’t headed in the right direction.

      • Kathy Comiskey

        ‘That map’ is published upside down. That’s why everything is going in the wrong direction. At our daughter’s wedding? I told everyone ‘Throw that out!’

        • Linda Grist Cunningham

          What a great story!

Related Posts

What does Key West look like? Depends on who’s doing the looking

What does Key West look like? Depends on who’s doing the looking

What does Key West look like? And we answer it every time a proposed renovation or major development project drop its AI-generated drawings, “But that doesn’t look like Key West.” I’m of the mind that Key West looks exactly like what we are, a weirdly cobbled together accumulation of architecture that changed each time residents felt flush with cash and an itch to expand.

What’s in a name? The new “old Publix” and the old “new Publix”

What’s in a name? The new “old Publix” and the old “new Publix”

You can stick up all the signs you want, even change U.S. maps, and folks are still going to call it the way they learned it. Take that quarter-mile concrete pier at the end of Key West’s White Street. Rebranded in June 2016 as the Edward B. Knight Pier, it remains the White Street Pier. Humans ain’t much fond of changing up words just for the heck of it. So what do we do with Old and New Publix?

Pin It on Pinterest