Seen through Ernest's eyes

The Florida Keys were a favourite of Hemingway – and they still enchant.

It was all Uncle Gus's fault. His botched delivery was enough to change the identity of an entire town – and alter the direction of modern American literature. The year was 1928 and the delivery in question was a new Ford Roadster. The intended recipient: a young writer named Ernest Hemingway.

Along with his second wife, Pauline (Gus's favourite niece), the 32-year-old Hemingway was travelling north from Cuba when he stopped at the western end of the Florida Keys in the town of Key West to take possession of the wedding gift. But the delivery was two weeks late, so the Hemingways were forced to sit it out here, at America's answer to Land's End. By the time the motor car finally arrived, Ernest's feet were well and truly under the table -primarily in a local bar called Sloppy Joe's -and he had fallen thoroughly in love with the little island town.

Today, Key West, the southernmost point in the continental USA, is known internationally as Hemingway's place. It was here that the Nobel Prize-winning author produced his greatest body of work over a ferocious nine-year period, as he fished, fought and drank his way around the island. And it's also here that the legacy of the great buccaneer-writer is kept alive -from the countless framed pictures of "Papa" hanging from the walls of bars and restaurants to the popular "Hemingway Days" festival every July.

You can see why Key West appealed so strongly to Hemingway's romantic soul. Dangling at the bottom of the long, slender Florida Keys like a shiny, golden pendant at the end of a hypnotist's chain: a magnet for mavericks, creatives and free spirits worthy of the nickname "SoHo in the Sun". The locals see it as separate and distinct not just from the rest of Florida, but the rest of the archipelago, referring to it as the Conch Republic.

Much of the glamour from Hemingway's heyday in the Twenties and Thirties remains, from the super-luxe (and surprisingly affordable Casa Marina hotel, to the beautiful Art Deco movie theatre at the heart of the old town, The Tropic, recently voted the best cinema in Florida. There are so many good restaurants in Key West that it's impossible to try them all in a week, while art galleries, museums and boutique shops cluster around the colourful gingerbread houses. Even Sloppy Joe's is still here, but don't be fooled by the tourist trap on Duval that's taken its name. The real Sloppy's, where Hemingway drank with his cohorts is now called Captain Tony's Saloon, and can be found at 428 Greene Street.

From here, Hemingway would regularly stagger home barefoot to his well-appointed house on Whitehead Street, often wearing nothing more than a pair of shorts with a piece of rope holding them up. The beautiful Key West lighthouse is directly across the street, with Hemingway joking that he chose the house so he had a beacon to navigate his way home after a heavy night's drinking. The family home was already becoming a visitor attraction during Hemingway's final years here, to the extent that he employed a leper to sit at the gate and scare them off. Today it's considerably easier to visit.

The stately, colonial-style building is still populated by dozens of the six-toed cats the deeply superstitious Hemingway bred for good luck and carried around like infants. But best of all, you can visit his studio above the coach house, where he would write every day from 6am -however bad the hangover -and worked on novels including To Have and Have Not and The Old Man and The Sea.

Drinking, sunshine and writing have always been at the heart of the Key West story. The place has attracted literary giants such as Tennessee Williams, Hunter S Thompson and Truman Capote. Capote is still revered for one particular night of drinking in a Key West bar. After a woman angered her husband by asking the author to autograph a napkin, the man approached Capote, "unzipping his trousers and hauling out his equipment". Many heard him say: "Why don't you autograph this?" to which Capote replied: "I don't know if I can autograph it, but perhaps I can initial it."

Today the town is still a literary haven, with more than 50 published authors based within its four-mile by one-mile area. Captain Tony's and Sloppy Joe's are both forgotten though, with local inky fingers now reaching for bar menus at Louie's Backyard -one of the finest restaurants in the whole of the Keys, with a lively outdoor cocktail area backing right onto the water.

Even the sunsets here are luxurious. Crowds gather in Mallory Square to applaud the sun go down over the ocean, while magicians, dancers and performing cats entertain them. The best way to experience a Key West sunset in true style, however, is from a jet ski. Local operator Barefoot Billy's offer a daily Sunset Tour, chasing the red sun around the entire island, as you accelerate into the rich, molten colours at 50mph.

Hemingway's favourite aquatic pastime, big-game fishing, is still big news here too. And you can experience it yourself by hiring one of the hundreds of fishing boats and captains in these parts. This is destination fishing at its very best and, like our host for the day, the improbably named Captain Randy Towe, your skipper will often clean and fillet your catch for you, delivering it to a local restaurant of your choice to be prepared in all manner of delicious ways.

A coral finger beckoning to the weird, wonderful and inspirational of America, the Florida Keys have an end-of-the-world feel that is as indulgent as it is unique. From the yachts to the high-end restaurants and bars of Key West, there's a real sense of class to proceedings, yet conversely there's nowhere you can't walk in wearing aT-shirt. It's easy to see why Hemingway fell in love with the place.

Ironically, it was love that took Hemingway away from here in the end. After meeting his third wife, the journalist Martha Gellhorn, he left the Florida Keys for Cuba. However, they say once Key West sand gets in your shoes you always come back, and that was true of its most famous adopted son too. He returned with his fourth wife Mary in the early 1960s, shortly before his death. More than 50 years later, many would say the King of the Conch Republic has never left.

Travel Essentials

Getting there

The main gateway to Key West is Miami, served from Heathrow by American Airlines, British Airways and Virgin Atlantic. You can either rent a car and drive the 160 miles from Miami airport to Key West at the far end of US Route 1, or transfer to a short commuter flight.

Eating there

Louie's Backyard (001 305 294 1061;

Pisces Key West (001 305 294 7100;

A&B Lobster House (001 305 294 5880; aandblobster

Azur (001 305 292 2987;

Drinking there

Captain Tony's Saloon (001 305 294 1838;

Nine one five (001 305 296 0669;

Vinos Wine Bar & Shop (001 305 294 7568;

The Porch (001 305 517 6358;

Experiencing there

Sunset Jetski Tour (001 305 900 3088;

Deep Sea Fishing with Captain Randy Towe (001 305 394 2667;

Staying there

The Ocean House at Islamorada (001 305 664 4844; has doubles from $302 (£189) per night, room only.

Hyatt Key West Resort & Spa (001 305 809 1234; offers double rooms from $362 (£226) a night, room only.

More information

Have you tried new the Independent Digital Edition apps?
ebookHow to enjoy the perfect short break in 20 great cities
Richard Blair is concerned the trenches are falling into disrepair
newsGeorge Orwell's son wants to save war site that inspired book
Life and Style
Audrey Hepburn with Hubert De Givenchy, whose well-cut black tuxedo is a 'timeless look'
fashionIt may be a paradox, but the industry loves it
Arts and Entertainment
The pair in their heyday in 1967
Life and Style
fashionFrom bathing dresses in the twenties to modern bikinis
Independent Travel Videos
Independent Travel Videos
Simon Calder in Amsterdam
Independent Travel Videos
Simon Calder in Giverny
Independent Travel Videos
Simon Calder in St John's
Independent Travel Videos
Latest stories from i100
Have you tried new the Independent Digital Edition apps?
Independent Dating

By clicking 'Search' you
are agreeing to our
Terms of Use.

ES Rentals

    iJobs Job Widget
    iJobs Travel

    Guru Careers: Events Coordinator / Junior Events Planner

    £24K + Excellent Benefits: Guru Careers: We are seeking an Events Coordinator ...

    Royal Yachting Association Cymru Wales: Chief Executive Officer

    Salary 42,000: Royal Yachting Association Cymru Wales: The CEO is responsible ...

    Guru Careers: Marketing Manager / Marketing Communications Manager

    £35-40k (DOE) + Benefits: Guru Careers: We are seeking a Marketing Communicati...

    Ashdown Group: Technical IT Manager - North London - Growing business

    £40000 - £50000 per annum: Ashdown Group: A growing business that has been ope...

    Day In a Page

    Abuse - and the hell that came afterwards

    Abuse - and the hell that follows

    James Rhodes on the extraordinary legal battle to publish his memoir
    Why we need a 'tranquility map' of England, according to campaigners

    It's oh so quiet!

    The case for a 'tranquility map' of England
    'Timeless fashion': It may be a paradox, but the industry loves it

    'Timeless fashion'

    It may be a paradox, but the industry loves it
    If the West needs a bridge to the 'moderates' inside Isis, maybe we could have done with Osama bin Laden staying alive after all

    Could have done with Osama bin Laden staying alive?

    Robert Fisk on the Fountainheads of World Evil in 2011 - and 2015
    New exhibition celebrates the evolution of swimwear

    Evolution of swimwear

    From bathing dresses in the twenties to modern bikinis
    Sun, sex and an anthropological study: One British academic's summer of hell in Magaluf

    Sun, sex and an anthropological study

    One academic’s summer of hell in Magaluf
    From Shakespeare to Rising Damp... to Vicious

    Frances de la Tour's 50-year triumph

    'Rising Damp' brought De la Tour such recognition that she could be forgiven if she'd never been able to move on. But at 70, she continues to flourish - and to beguile
    'That Whitsun, I was late getting away...'

    Ian McMillan on the Whitsun Weddings

    This weekend is Whitsun, and while the festival may no longer resonate, Larkin's best-loved poem, lives on - along with the train journey at the heart of it
    Kathryn Williams explores the works and influences of Sylvia Plath in a new light

    Songs from the bell jar

    Kathryn Williams explores the works and influences of Sylvia Plath
    How one man's day in high heels showed him that Cannes must change its 'no flats' policy

    One man's day in high heels

    ...showed him that Cannes must change its 'flats' policy
    Is a quiet crusade to reform executive pay bearing fruit?

    Is a quiet crusade to reform executive pay bearing fruit?

    Dominic Rossi of Fidelity says his pressure on business to control rewards is working. But why aren’t other fund managers helping?
    The King David Hotel gives precious work to Palestinians - unless peace talks are on

    King David Hotel: Palestinians not included

    The King David is special to Jerusalem. Nick Kochan checked in and discovered it has some special arrangements, too
    More people moving from Australia to New Zealand than in the other direction for first time in 24 years

    End of the Aussie brain drain

    More people moving from Australia to New Zealand than in the other direction for first time in 24 years
    Meditation is touted as a cure for mental instability but can it actually be bad for you?

    Can meditation be bad for you?

    Researching a mass murder, Dr Miguel Farias discovered that, far from bringing inner peace, meditation can leave devotees in pieces
    Eurovision 2015: Australians will be cheering on their first-ever entrant this Saturday

    Australia's first-ever Eurovision entrant

    Australia, a nation of kitsch-worshippers, has always loved the Eurovision Song Contest. Maggie Alderson says it'll fit in fine