“Cayos”, was the word used by Spanish navigators to name the archipelago of small islands that drifted southwest towards the Caribbean. Over time, the cayos have adapted and Americanized to the Keys.
Route 1 brings cars from Miami. The skeleton of the epic Flagler Railroad, destroyed by the Labor Day hurricane of 1935, sweeps across the islands and sea. Or visitors can fly into Key West Airport.
Finally, at the southernmost point of the United States, Cuba, just 90 miles away, is closer than Miami. Roosters strutting the sidewalks of Key West, released in protest by their Cuban owners when cockfighting was banned, showcase Cuban heritage.
Not only is Key West different because it’s the only American city to never experience freezing, but the city has a wacky left-field feel. After harsh police measures harmed tourism, in 1982 the Conch Republic declared independence and war on the United States. State officials were bombarded with stale buns.
Too quirky to be Stars and Stripes Florida and too northern to be true Caribbean, the people of Conch like to compromise with the Floribbean label.
Visitors must choose how they will explore a Key with the laid-back aura of yesteryear: bike ride, gourmet stroll, rum tasting, catamaran at sea or the eternal favorite of…
1. The conch train
Riding the Conch Train, which has been criss-crossing the city streets since 1958, is a great introduction to Key West. A local driver’s commentary not only helps visitors learn about the orientation of the city, but also learn about the history of Key West.
The passage through the upper rooms of the coastal houses partly explains the wealth of Key West. Shipwreckers watched from above for stranded ships. Then it was a wreckage race as the first on the spot could claim 50% of the salvage value. Shipowners took 25% while the city took advantage of the remaining 25%.
2. Ernest Hemingway’s house
A delay in the delivery of a Ford car to Ernest Hemingway forever changed the history of Key West. While waiting for the car, writer and second wife Pauline falls in love with Key West.
A visit to Hemingway’s home reveals Hemingway’s most productive years as a novelist. Then, covering World War II in Europe, Hemingway meets Martha Gelhorn. Eventually, she became his third wife.
To protest the affair, Pauline demolished Hemingway’s boxing ring and spent $20,000 of his money in a swimming pool. After Hemingway threw a penny at her, shouting that she might as well take “her last penny”, she placed the red penny in the poolside.
The poolside is a favorite sunbathing spot for descendants of Hemingway’s original six-toed cat.
3. Duval Street
Many visitors to Key West seek out the spirit and spirits of Hemingway among the many bars, sometimes three stories high, along Duval Street.
Writing 700 words in the morning, fishing for marlin in the afternoon, Hemingway was drinking on Duval Street in the evening. Follow the beam from the lighthouse, next to his house, to find the way back.
Tennessee Williams added another layer of literary history when he stayed on Duval Street to work on A tram called Désir.
4. At sea
Often the best way to see the Keys isn’t on the Keys but from the sea: paddling a canoe through the swamps, viewing sea life from a glass-bottom boat, or sailing aquamarine seas on a catamaran. Snorkeling in shallow warm waters is an easy way to see schools of colorful tropical fish around the reef in the Florida Keys.
Big game fishing, in the wake of Hemingway The old Man and the Sea, is another classic Key West challenge. Winner of both the Pulitzer Prize and the Nobel Prize for Literature, Hemingway in his last great novel wrote about Santiago, a fisherman who goes 84 days without catching a marlin. It’s a poignant story that foreshadows Hemingway’s own decline.
Key West has its only distinct tap-dancing architecture: hints of New England, echoes of the Bahamas. The wraparound porches are ideal for rocking chairs and sipping mint juleps. The light pastel tropical design and classic colonial architecture blend nicely in Key West.
Eyebrow houses are part of the neo-classical style whose awnings hide the windows of the top floor, like the eyebrows, they protect the rooms from the heat and deepen the shade on the porch.
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6. The Little White House
As President of the United States from 1945 to 1953, Key West became Harry Truman’s escape from Washington. His doctors recommended a warmer climate, a morning dose of Bourbon “to get his heart going” and a two-mile walk.
A tour of the house reveals Truman’s casual Hawaiian shirt wardrobe, a departure from his usual formal dress elegance as a former haberdasher. A tape recording also reveals that Truman was an accomplished pianist.
Almost everyone, including some of the street performers and a few souvenir vendors, stop for sunset in Key West, as a blood-red sun fades to shades of orange on the horizon.
It’s an almost spiritual moment, sometimes over a soundtrack of steel drums and almost always over cocktail ice cubes.
As night falls and the aromas of fried seafood drift through the warm air, it’s time for dinner, followed almost inevitably by a silky and tangy key lime pie.
8. Heart and soul
Maybe it’s away from the traditional United States, maybe it’s the proximity to the Caribbean. Perhaps it is surrounded by Flipper territory. Somehow, Key West has clung to its heart and soul, earning a reputation as a haven where laid-back folks sip their Cuban coffee, iced tea, or margarita.
Disclosure: Our tour of Key West attractions was sponsored by The Florida Keys and Key West.
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