8 reasons to visit Key West, Florida, USA /

“Cayos” was the word Spanish navigators used to name the archipelago of small islands drifting southwest toward the Caribbean. Over time, cayos have been adapted and Americanized to the Keys.

Route 1 brings cars from Miami. The skeleton of Flagler’s epic railroad, destroyed by the 1935 Labor Day hurricane, scans islands and sea. Or visitors can fly into the Key West airport.

Finally, at the southernmost point in the US, Cuba is just 90 miles away, closer than Miami. Roosters that parade the sidewalks of Key West, released by their Cuban owners when cockfighting was banned, emphasize Cuban heritage.

Not only is Key West different because it’s the only city in the US where it never freezes, the city also has a wacky left-wing feel. After heavy-handed police action damaged the tourist trade, the Conch Republic declared independence and war on the US in 1982. State officials were pelted with old sandwiches.

Too quirky to be Stars and Stripes Florida and too far north to be truly Caribbean, Conch people like to compromise with the Floribean tag.

Visitors must choose how they want to explore a Key with a laid-back feel of yesteryear: bike ride, foodie tour, rum tasting, catamaran out at sea, or the perennial favourite…

1. The Conch Train

Taking the Conch Train, which has been cruising the city streets since 1958, is a great introduction to Key West’s low-rise buildings. Commentary by a local driver not only helps visitors learn the city’s orientation, they also get a potted history of Key West.

Passing high rooms in coastal homes partly explains Key West’s wealth. Shipbreakers watched from above for ships that had run aground. After that it was a race to the wreck, because the first one there could claim 50% of the residual value. Shipowners took 25%, while the city benefited from the remaining 25%.

2. Ernest Hemingway’s house

A delay in the delivery of a Ford car to Ernest Hemingway changed Key West history forever. While waiting for the car, the writer and second wife Pauline fell in love with Key West.

A visit to Hemingway’s home reveals Hemingway’s most productive years as a novelist. Next, Hemingway, covering World War II in Europe, brings in Martha Gelhorn. Eventually she becomes his third wife.

In protest of the affair, Pauline tore off Hemingway’s boxing ring and spent $20,000 of his money on a swimming pool. After Hemingway threw a penny at her, yelling that she might as well take “his last penny”, she placed the red penny in the edge of the pool.

The pool is a favorite sunbathing spot for the descendants of Hemingway’s original six-toed cat.

3. Duval Street

Many a Key West visitor searches for the ghost and ghouls of Hemingway among the many bars, sometimes three stores high, along Duval Street.

He wrote 700 words in the morning, fished marlin in the afternoon, and drank on Duval Street in the evening. Follow the beam of the lighthouse, next to his house, to find his way home.

Tennessee Williams added another layer of literary history when he stayed on Duval Street to work on A street car named Desire.

4. At sea

Often the best way to see the Keys is not on the Keys, but from the sea: paddling through the marshes in a canoe, watching the marine life from a glass-bottomed boat, or sailing the aquamarine seas on a catamaran. Snorkeling in shallow warm water is an easy way to view schools of colorful tropical fish around the Florida Keys Reef.

Deep-sea fishing, in Hemingway’s footsteps The old man and the sea, is another classic Key West challenge. Hemingway won both the Pulitzer Prize and the Nobel Prize for Literature and in his last great novel wrote about Santiago, a fisherman who does not catch a marlin for 84 days. It’s a gripping story that foreshadows Hemingway’s own demise.

5. Architecture

Key West has its one distinct clapperboard architecture: hints of New England, echoes of the Bahamas. Wraparound porches are great for rocking chairs and drinking mint juleps. Light pastel tropical design and classic colonial architecture come together pleasantly in Key West.

Eyebrow houses are part of the Classical Revival style whose canopies hide the windows on the top floor, like eyebrows they protect rooms from the heat and deepen the shade on the porch.

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6. The Little White House

Key West served as US President from 1945 to 1953 and became Harry Truman’s getaway from Washington. His doctors recommended a warmer climate, a morning shot of Bourbon “to get his heart going,” and a two-mile walk.

A tour of the house reveals Truman’s relaxed wardrobe of Hawaiian shirts, a break from his usual formal sartorial elegance as a former shopkeeper. A tape recording also reveals that Truman was an accomplished pianist.

7. Sunset

Nearly everyone, including some street performers and some souvenir peddlers, pause for the Key West sunset as a blood-red sun fades to orange hues on the horizon.

It’s a quasi-spiritual moment, sometimes set to a soundtrack of steel drums and almost always over clattering cocktail ice.

As darkness falls and the aromas of fried seafood waft through the warm air, it’s time for dinner, followed almost inevitably by silky, tangy Key Lime Pie.

8. Heart and soul

Maybe it’s the distance from the mainstream US, maybe it’s the proximity to the Caribbean. It may be surrounded by Flipper territory. Somehow, Key West has clung on with heart and soul, earning a reputation as a laid-back getaway where laid-back people sip their Cuban coffee, iced tea, or margarita.

Disclosure: Our visit to the Key West attractions was sponsored by The Florida Keys and Key West.