Hemingway’s Favorite Getaway Is an Adventurer’s Dream

Kitesurfing, spearfishing, and plenty of great food await in one of Florida’s most famous beach destinations.

Hemingway’s Favorite Getaway Is an Adventurer’s Dream

Courtesy of Pixabay

Key West is bouncing back from Hurricane Irma. While work still remains cleaning up debris and rebuilding properties along the coast, Hemingway’s favorite hideaway is once again open for business. And for thrill seekers, it’s the place to be. New opportunities for adventure tours are shifting Key West’s reputation as a haven for drunk tourists and sleazy bars. Instead, the focus now is sandbars, sponge flats, and the colorful (not to mention delicious) marine life. Ready to dive in? Read on.

Try your hand at kiteboarding

Kiteboarding, aka kitesurfing, which involves having your feet strapped onto a board while a wind-harnessing kite pulls you across the water, isn’t for the faint of heart. So who better to learn from than a Guinness World Record holder in the sport? Key West native Paul Menta has been at it since the late 1990s and knows these waters well. One of his favorite spots to teach is Smathers Beach, a pristine, palm-lined shore close to the airport. You can wade out for 15 miles and still be knee-deep in water, making it perfect for beginners who—understandably—may struggle to stay upright.

Hunt for your dinner

Can’t seem to catch the wind? Maybe you’ll have better luck catching your dinner. Spearing a snapper or a lobster takes considerable skill and patience, but with all that incredible marine life wriggling around down there (manatees, sea turtles, reef sharks, spotted eagle rays), the adrenaline rush alone is worth the trek. Finz Dive Center, known for its spectacular nocturnal dives, offers a four-hour chartered, all-inclusive spearfishing tour that brings you out to deep-water reefs chock-full of fish. At the end, the instructors will even help you clean and fillet your catch—talk about fresh!

Go far from the crowds

In the remote wilderness of Mud Key, roughly 30 minutes by boat from Stock Island, you’ll get to paddle through clearwater streams that crisscross through dense mangrove forests. Eco-tour guide Sera Sullivan, who leads spearfishing expeditions at the newly built Oceans Edge Resort, refers to this as Key West’s “backcountry” and says she finds “serenity in every moment [spent] floating in this incredible paradise.” Best of all, you won’t run into any crowds: Thanks to its name, hardly any tourists come out this way.

Refuel after the adventure

When you’re not on the water, fuel up in style. In downtown Key West, Caroline’s Other Side is a 1950s-era cocktail bar tucked in the back parlor of a mansion on Caroline Street. Two blocks away, you can slurp oysters or dig into fennel-infused lobster cakes at Thirsty Mermaid, which boasts the town’s only locally sourced raw bar. After catching a provocative performance by Key West Burlesque, end your evening at Mary Ellen’s, a sports bar with gourmet sensibilities; in the back, you’ll find a (not-so-)secret takeout window serving up imaginative twists on grilled cheese. After all that paddling, you deserve it.

Alex Schechter is a Los Angeles–based writer who loves forests, hot springs, and posole. His writing has appeared in the New York Times, AFAR, Travel+Leisure, Monocle, and LA Yoga, among other publications.
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