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Best of Key West - Ten things you mustn’t miss when visiting the southernmost point of the USA

By Martin Li

Last Resort

The Overseas Highway to Key West follows a trail originally blazed in 1912 when Henry Flagler extended his railroad from Miami to the last of the Florida Keys. A hurricane destroyed the railroad in 1935 but the highway survives to provide a dramatic experience of driving over the sea. Drive slowly to appreciate fully the beauty of this marine wilderness which spans 42 bridges, including the famous Seven Mile Bridge.

Secede, Don’t Fail

Take time to do nothing but savor the unique end-of-the-road atmosphere of Key West which, whilst separated from mainland Florida by only 100 miles, is attitudinally a world apart. Long a haven for wreckers, writers, artists and adventurers, the island is a melting pot of cultures and influences united by an easygoing irreverence. President Truman was so enchanted by Key West he declared: “I’ve a notion to move the capital to Key West and just stay”. The island had other ideas and declared itself the independent “Conch (pronounced “conk”) Republic” in 1982.


Join visitors and islanders as they celebrate sunset each evening at Mallory Square, the historic pier overlooking the Gulf of Mexico. This waterfront carnival features colorful jugglers, musicians, fortune tellers, street vendors and craftspeople. A kilted bagpiper plays. A tightrope walker balances high above the crowd.  The “Cookie Lady” sells home-made brownies from her bicycle basket. For the best view of the festivities, arrive at least half an hour before sunset. Alternatively take a sunset sail on a tall ship like the Schooner Wolf and let the creaking of the rigging evoke the ghosts of Key West’s seafaring past.

Show Time

Hardly a weekend goes by without a special event or festival. The tongue-in-cheek Independence Celebration on April 23 celebrates the island’s mock secession from the USA. Hemingway Days is a week of nostalgia commemorating the author’s July 21 birthday with look-alike contests, short story competitions, writing workshops and competitions. The October Fantasy Fest is a lavish mardi gras incorporating costume balls, a Masquerade March, street fair and a spectacular parade of floats. Old Island Days runs from November to May and includes art and craft shows, theatre, music, pageants and conch shell blowing contests.

Creative Spirits

Explore the waterfront restaurants, ramshackle wooden bars and shops of the historic seaport district. Unmissable is a drink at Sloppy Joe’s Bar where Ernest Hemingway spent many an afternoon with his cohorts. Also walk through the quiet streets of the predominantly wooden Old Town with its Victorian houses with wraparound verandahs, pastel cottages and tall palms.

Civil Turncoats

Many Key West residents were southern sympathizers during the Civil War, but changed allegiance after waking one morning to find their island occupied by Union forces. Take a ferry or seaplane and visit the atmospheric Fort Jefferson in the Dry Tortugas, a group of tiny islands 70 miles from Key West.  Fort Zachary Taylor on Key West has an impressive collection of cannons and its Civil War Days event each February re-enacts historic battles.

Curious Cats

Hemingway wrote many of his best-known works in the second-floor studio adjoining his former Key West home. The colonial villa is now an evocative living museum honoring the island’s most celebrated writer. While walking the grounds, make friends with the many six-toed cats supposedly descended from Hemingway’s own beloved felines.

Determined Diver

The treacherous waters surrounding the keys made Key West the mecca of wreck salvagers throughout the last century. In 1985, following a 16 year search, Mel Fisher finally discovered the $400 million treasure of the Spanish galleon Nuestra Senora de Atocha. The Mel Fisher Maritime Museum exhibits gold, silver, jewels, religious artefacts, rare navigational instruments and weapons from this and other local wrecks.  If you prefer watersports first-hand, skippers at the harbor will take you to world class diving on living coral reefs and abundant deepwater fishing.

Dirty Dining

You’ll find the best Cuban sandwiches at little stands at the island’s laundromats.  Blue Heaven in the revitalized Bahama Village serves great breakfasts, Caribbean specialities and has roosters wandering between its tables. Key Westers not only honor but also love to devour their favorite pink mollusk, conch specialities including lime salad, spicy chowder and deep-fried fritters.  Join the conch fest and afterwards try Key Lime Pie, the island’s signature dish, which should be yellow in color and not green.

Cryptic Tales

Even death does little to dampen the irreverence of Key West residents. Visit the cemetery in the heart of the historic district and read the humorous epitaphs which include “I Told You I Was Sick”, “At Least I Know Where He’s Sleeping Tonight” and “The Buck Stops Here”. The cemetery is strangely picturesque with stone-encased caskets resting above ground, shaded by tropical trees and circled by meandering paths.

Martin Li is a freelance travel and lifestyles writer based in London. Born in Hong Kong, his family moved to London when he was three. After graduating from Cambridge University with a degree in physics, Martin worked initially in high level positions in financial services and capital markets.  Martin has published a number of books and articles and his topics frequent include his parchment for hideaways destinations, adventure trips, and sports travel. (More about this author).

Martin Li


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