by | February 4, 2026

Feel the Thrill in the Florida Keys

How a former pro kiteboarder turned the Florida Keys into an adventurer’s dream.

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The Florida Keys is a water-sport paradise. Photography courtesy of Visit the Florida Keys.

After launching off a 10-foot wave during a storm, action sports athlete and former pro kiteboarder Matt Sexton came crashing down—right onto a hidden rock. The impact shattered his foot. Months later, a second accident broke the other. For nearly a year, he couldn’t walk.

But Sexton doesn’t quit. He adapts.

Today, Sexton channels that same fearless energy into running Grassy Flats Resort & Beach Club and The Lagoon in Marathon, turning the Florida Keys into his personal playground for kiteboarding, wakeboarding and more.

“Action sport is an endorphin boost and is extremely satisfying,” he says. “Hospitality, for better or worse, can have the exact same responses for you but just a little bit more delayed.” And there’s no better place to chase the rush than the Florida Keys.

Since 2005, Sexton, a New England native, has called this 125-mile island chain home, drawn to its wild waters, rich ecosystems and nonstop adventure. One week this fall, he caught a 50-pound wahoo off Marathon. Days later, he dove into a school of 30 more—each appearing to weigh 30 to 70 pounds. On a single free dive near a wreck, he spotted wahoo, rainbow runners, African pompano and more. And that’s just the Middle Keys.

Up in Islamorada, known as the Sportfishing Capital of the World, anglers can tap into an unmatched variety of marine life. Between Mile Markers 79 and 83, the blend of flats, channels and deep offshore waters creates ideal conditions for everything from tarpon to sailfish.

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Go offshore fishing for mahi in the Florida Keys. Photography of Visit the Florida Keys.

Further south, the Lower Keys offer a different kind of magic. Stretching from Key West to the Seven Mile Bridge, this backcountry paradise is shallow, serene and largely untouched—dotted with soft sand, coral flats and uninhabited mangrove islands. It’s one of the Keys’ most private, pristine spots.

“No matter what you’re chasing in the outdoors, you can make it happen here in the Keys,” Sexton says. “There’s a lot of variety. Depending on where you go, there’s something for everyone.”

Underwater explorers can dive into the Florida Keys National Marine Sanctuary’s trail of nine historic shipwrecks, scattered across coral reefs and sandy shallows. For a heart-pounding challenge, Sexton recommends spearfishing wahoo—fast, powerful and wildly elusive.

At The Lagoon on Grassy Key, Sexton and his team offer a full lineup of action sports, including kiteboarding, foil boarding and wakeboarding. Their guests range from what Sexton calls the “boardroom warriors of Silicon (Valley) and Wall Street” to weekend adventurers and first-timers seeking a rush.

“The further you get from everyone else, the better everything feels,” Sexton says half-joking, half-serious.

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Scuba dive colorful coral reefs off the coast of the Keys. Photography courtesy of Visit the Florida Keys.

For Sexton, kiteboarding is still the ultimate escape. “It’s as good as it gets,” he says. With endless terrain, consistent winds and waves just yards apart, the Keys are the perfect playground for a former pro chasing the next thrill.

Whether you’re flying across the water, reeling in a trophy fish or paddling through untouched mangroves, the Keys deliver something rare: endless ways to discover wild Florida.

Ready to dive in? Go to visitfloridakeys.com.


For more about the Florida Keys, click here.

About the Author

Nila is an award-winning journalist and editor whose work has appeared in Condé Nast Traveler, Garden & Gun and The New York Times, to name a few. Simon has written for Flamingo since 2017, with profiles on tennis star Sloane Stephens, the unique South Florida community of Stiltsville and the state’s best wellness resorts.