Key West, FL — Thanks, Henry Flagler. Maybe I’m 100 years too late, give or take a few, but if not for the foresight of this early 20th-century oil tycoon, the Overseas Railroad would not have been built. Flagler financed and built the railway linking mainland Florida to the islands of the Keys; the project was begun in 1905 and completed in 1912. The railroad operated until 1935, when a ferocious Labor Day hurricane blew the train from its tracks and destroyed much of the line.

Glen, what’s your point, you ask? Well, after the hurricane, the state of Florida acquired the right-of-way and rebuilt the whole thing as a roadway; it reopened in 1938 as the Overseas Highway, now designated US Route 1.  I think it’s one of the best rides in the state; indeed, “2 Wheels to Paradise.” Sure, it’s a straight and narrow 127-miles, but its 42 bridges cross some of the bluest water and clearest skies you’ll find in Florida. Key West, at the end of the line, is known for a funky, Caribbean vibe and offbeat people (and I mean that in a good way). The 50s-era wooden sign outside the Monroe County Courthouse welcomes visitors to “The end of the rainbow, and end of the route. Key West, Florida. Unlimited Opportunities, Tropical Vacationland.” Gotta love the optimism. In Key West, wild chickens roam the streets, protected by city statute (a friend who lives in the town tells me the chickens are the source of much local hilarity, “Has anyone seen my cock?” being a favorite saying).

In any case, Key West culture is certainly unique. Locals call themselves “Conchs” (pronounced KONKS). In 1982 the fierce individualists of the city issued a proclamation seceding from the Union and establishing themselves as the Conch Republic. Then they promptly surrendered and demanded foreign aid. Great move!

Many famous residents have graced Key West over the years. Ernest Hemingway spent much of the 1930s drinking, writing, drinking, fishing, and drinking here. Sloppy Joe’s and Captain Tony’s both claim to be Hem’s favorite watering hole. Tennessee Williams, Robert Frost, and Jimmy Buffett have also called the island home.

Up and down Duval Street in the historic heart of Old Town Key West, you’ll find bars, restaurants, cafés, galleries and more. Each evening, locals and tourists gather at Mallory Square for a sunset celebration; the tightrope walkers, fire jugglers, and cats-jumping-through-burning-hoops street performers working for tips are as much a part of the scene as the setting sun.

A sign on a fence in front of a house in Old Town reads: “The purpose of life is to fight maturity.”  It’s a slogan I always take to heart, and a ride to the Keys is a great way to live it.

FOR MORE INFORMATION: The Florida Keys by Motorcycle

Florida Keys Tourism Council:

Key West Chamber of Commerce:

I’ve written a couple of magazine articles about trips to the Keys ; first in 2004 for American Iron, and last year for RoadBike.  AAA’s Going Places picked up that article and ran a shorter version in the November/December 2010 issue .

Hemingway House

Mallory Square

About Glen Abbott
Glen Abbott is a Florida-based travel writer & photographer specializing in motorcycle touring and travel. He is regular contributor to Harley-Davidson's HOG Magazine, and his travel features appear regularly in motorcycle magazines and other publications.

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  1. Cathy Sweeney

    January 19, 2011

    Wow – that sure looks like a great trip! I didn’t know that the roadway had once been a railway — thanks for the education.
    Cathy Sweeney recently posted..On Location in Montmartre

  2. Travelin' Gringo

    January 19, 2011

    Thanks for all the great comments everyone!

  3. eat-laugh-love-anon

    January 19, 2011

    Wow, what a place!
    It has all the makings of a wonderful holiday — motorbikes (doing it your way), blue ocean, whacky locals and a bit of history.
    I reckon I could spend the best part of a decade “drinking, writing, drinking, fishing, and drinking” there… if there wasn’t so much else of the world to see!
    eat-laugh-love-anon recently posted..A Mini-Me Hot Pot

  4. greg urbano

    January 18, 2011

    i still have not made it to the keys, i gotta get there this year!
    greg urbano recently posted..The Brooksville Raid Reenactment – The Battle

  5. John in France

    January 18, 2011

    I know this area as well as Nicaragua – i.e. not at all. Thanks for your article!
    John in France recently posted..French Film Festival 2011 – Vive la différence!

  6. Brenda Hopkins

    January 18, 2011

    Born in Miami married a Key Wester in 1963, lived there 29 years and didn’t appreciate it unitil years after I left in 1992. Living in central fla. now but the rock still calls me home everyday…no place like it in the world..

  7. Charles McCool

    January 18, 2011

    Love, love, LOVE the Keys. Was there last October and will be there again in April. Cannot wait. Thank you for the pictures to hold me over…
    Charles McCool recently posted..Finding Cheap Flights- Airfarewatchdog

  8. jade

    January 18, 2011

    Great photos! This was always a fun trip from Jacksonville that we took as kids with our parents. And i’m pretty sure I have that same mermaid photo!
    jade recently posted..Kate Middleton should get married here

  9. Jeremy B

    January 18, 2011

    The keys are a fascinating part of Florida. The bridges offer great views and it definitely is a culture all its own down there!
    Jeremy B recently posted..Travel Tuesday question of the week – what’s your most embarrassing travel moment

  10. RumShopRyan

    January 18, 2011

    Ah…Key West. One of my favorite places. I’ll be driving down the overseas highway next month again and looking forward to it. You can find me posted up at Irish Kevins and Hogs Breath most of the time.


  11. Cam

    January 18, 2011

    Always wanted to visit the Keys. Now I want to even more! 😉
    Cam recently posted..City Spotlight – Brasov- Romania

  12. ayngelina

    January 18, 2011

    That mermaid sign is AWESOME.
    ayngelina recently posted..Would you buy a 500 turkey AKA Have you met Andres

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