Imagine a place so colorfully alive it’s inspired the works of both Jimmy Buffett and Ernest Hemingway: two artists who couldn’t be further from each other on the creative spectrum. At the very end of the Overseas Highway — a stretch of road that snakes all the way from Maine to the Florida Keys — you’ll find a tiny chain of islands that ends at Mile Marker 0.
Key West is the southernmost city in the continental U.S., a land of coconuts, coral reefs and trained circus cats. And if you think that sounds a little off-the-cuff, you’re not wrong.
Maybe it’s the heat. Maybe it’s all that fried conch. Or maybe there’s just something in the water. Whatever it is, there’s just something about Key West that makes you want to stay for good.
Here, five ideas on how to spend your time in Conch Country (whether you’re a fan of Hemingway or his margarita-loving counterpart).
Go off-shore fishing
Just 45 minutes north of Key West is Big Pine Key, a quieter island known for its fishing culture.
Whether you bring your own boat or charter one, Lower Keys fishing is not to be missed. Once your line is in the water, you’ll catch everything from yellowtail to grouper, sailfish to tarpon, mahi-mahi to snapper.
Just be prepared for the sun, and protect yourself with plenty of water, performance fishing shirts and giant straw hats.
Speaking of fishing, Ernest Hemingway found solace and inspiration in the sport when he lived and worked from Key West. In 1938, he caught a world-record seven marlin in one day. Another time, he landed a giant 468-pound marlin in just 65 minutes. His sport-fishing escapades inspired one of his most famous works, The Old Man and the Sea.
Visit the Hemingway House
Pulitzer Prize-winning author Ernest Hemingway left quite a legacy in Key West, and you can hear about all about the legends at the Hemingway Home, a house built by a salvage wrecker in 1851 and later lived in by Hemingway.
There are personal touches everywhere, from his big-game hunting trophies to the massive swimming pool one of his disgruntled wives built there to replace his beloved boxing ring.
Keep an eye out for the 40-some six-toed cats who live there, all descendants from a feline Hemingway was gifted by a sea captain.
It’s definitely worth waiting around for a free tour of the house.
Go for a hike
Wake up early before the heat and humidity set in and take a walk at the National Key Deer Refuge (key deer are dog-sized whitetails, an endangered species that can only be found here) or Blue Hole — both offer the chance to see snakes, alligators and native birds.
Explore Downtown Key West
They say it’s Austin we need to keep weird, but nothing can compare to the wackiness of downtown Key West.
From trucks encrusted with fake coral reefs to fresh seafood meals practically plucked from the sea in front of you, there’s nothing dull about this town. Wait in line to take a picture at the Mile Marker 0 sign or check out the distasteful shirt shops on Duval Street. If you’re more into art, visit the Wyland Gallery or swing by the true Margaritaville.
Then, head over to the daily Sunset Celebration at Mallory Square Dock, where you can drink freshly cracked coconuts, deep-fried conch, watch the street performers and catch a show from Dominique the Cat Man, who has trained his feline actors to walk on tightropes and jump through fire. His eccentric, over-the-top and baffling show is not to be missed.
Snorkel or dive the coral reefs
The Florida Keys are home to the only living coral reefs in the continental U.S., and they are teaming with life.
Every snorkel company boasts they know where the best reefs are, but you can’t go wrong with a visit to the Looe Key area, a protected marine life sanctuary where you’ll see Elkhorn and Star coral, sea turtles, blue tang, barracuda, spotted eagle rays and if you’re lucky, a dolphin or bull shark.
Snorkel trips leave out of Bahia Honda State Park daily.
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