Florida, Newsletter, North America, Trip Reviews, USA

Insider Guide to Key West, Florida, USA  

14/03/2023 by .
guide to key west

Michael Edwards offers up his insider guide to Key West as he visits the self-proclaimed Conch Republic

Closer to Cuba than Miami, Key West feels a world away from corporate Stars and Stripes America. Swimmers have even been tempted to swim those 90 miles between Cuba and the United States’ southernmost point. Usually, they swim in a shark-proof cage. But that doesn’t exclude the jellyfish.

Chickens strutting the streets, unofficial Key West mascots, recall Cuban heritage. When cockfighting was banned in the 1970s, Cuban immigrants released their chickens onto the streets in protest. Given their freedom, the chickens thrived.

Smathers Beach 1

Getting their cayos name from the Spanish for small islands, cayos became corrupted to keys. Key West is the final and most westerly island in a long archipelago of islands that curves towards Central America.

You can fly into Key West airport, but many visitors take the road trip from Miami down Route 1 to the much-photographed – and oft-stolen – 0-mile route marker at the heart of Key West. Long bridges link a succession of small islands, often following the spine of Flagler’s railroad destroyed by the ferocious hurricane that hit on 1935’s Labour Day. It took Key West a long time to truly become connected to mainland USA.

Key West Conch Train

An essential component of this insider guide to Key West is the Conch train tour. Commentary on The Conch train, rolling through the city’s streets since 1958, reveals that at times Key West has been a reluctant member of the USA. Back in 1982 when heavy US policing had a negative impact on tourism, Key West declared both independence and war, attacking US officials with stale bread rolls. Tongue-in-cheek, some Key West folks argue that the letter of secession was never revoked and that the Conch Republic is independent.

Key West 1

As the only US city never to suffer a frost, sitting pretty somewhere between the Caribbean and Florida, the locals like the Florribean tag. Particularly around sunset when rum cocktails flow, when steel drums provide the soundtrack for street entertainers. Crowds gather around Mallory Square, almost in spiritual reverence, as the sun sinks into the sea.

White clapperboard and pastel-shade homes have hints of both Caribbean and New England architecture. Wrap-around porches are perfect for sitting in a rocking chair and sipping iced tea or a mint julep. On eyebrow houses, extended awnings act like eyebrows, shading windows.

Sebago sunset cruise

Along the southern coast, the sturdy houses, often built with ship-building techniques to protect against hurricanes, often have one room set on high. Here those who made their dollars from shipwrecks, peered through their telescopes for the latest ship to run aground. First one to reach the ship could claim 50% of its salvage value. The original owners got 25% and Key West city took the remaining 25%. Visit the Key West Shipwreck Museum for the full story.

No insider guide to Key West would be complete without mentioning Hemingway.  For decades, the Ernest Hemingway legacy has attracted visitors to tour the novelist’s house looking out for the cats who are descendants of Hemingway’s original six-toed cat. As a man who was wounded in the First World War and survived a plane crash whilst on safari in Africa, superstitious Hemingway hoped that his cat would bring good luck.

Hemingway house

The novelist was at his happiest and most productive during his Key West years. Writing 700 words in the morning, fishing for marlin in the afternoon and drinking in the evening. Finally finding his way home, guided by the beam from the nearby lighthouse.

Hemingway’s tales of reeling in 90-pound marlin, sometimes in less than an hour, and his The Old Man and the Sea novel inspire visitors to head for some deep-sea fishing.

duval street

Other visitors follow in Hemingway’s footsteps to Duval Street. As some buildings house three bars stacked on top of each other, at times Duval Street has housed over 200 bars. Be aware that in the Garden of Eden Bar, on the top floor of The Bull and Whistle, clothing is optional.

Pauline, Hemingway’s second wife furiously pulled down his boxing ring when she discovered that whilst reporting on the liberation of Europe in 1944, her husband had begun an affair with reporter Martha Gelhorn.  Hemingway returned to Key West to discover that Pauline had spent $20,000 of his money on a swimming pool. Putting it in an economic context, the hotel had only cost them $8,000. He furiously threw a cent at her, shouting that she might as well take his last penny. She accepted the red penny and had it set in the pool surrounds. It is still there today.

Hemingyway pool

A tour of The Little White House reveals the story of Key West’s second most famous visitor. President Harry Truman, serving from 1945 to 1953, was advised by his doctor to seek warmer climes for his health. Nicknamed The Haberdasher, after his pre-politics career, the sartorially elegant Truman spent around 10% of his presidency in Key West. Beginning every day with a shot of bourbon, as advised by his doctor, to get his heart going.

Many argue that the best way to see the Keys is not on the Keys but from the sea. Glass-bottom boats, catamarans, and snorkelling, all explore the tropical marine life on the Florida reef. Back on land the Key West Aquarium also displays many marine species.

Honest Eco


Landlubbers may prefer to hire bikes to explore at their own pace, while others opt to take a foodie tour that really ought to include Key Lime pie. Or in the true spirit of Hemingway, there is always rum tasting.


Tell Me More About this Insider Guide to Key West, Florida


for more information on a guide to Key West visit Florida Keys Tourism Information for all the insider information you will need to plan a visit.

Flights to Key West from London begin from around £500, travelling via New York USA. Alternatively from around £450, fly direct to Miami. Then hire a car for the 160-mile drive to Key West. 





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