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A Locals' Guide to the Florida Keys

We asked five of the Keys' most intrepid residents for their favorite outings, eateries, and watering holes

(Photo: Cody Spinadel)

Even if you’ve never been to the Florida Keys, you can probably conjure an image of life on Florida’s crescent-shaped archipelago—people lazing in hammocks, frozen cocktails in hand, palm trees swaying in the breeze. And while that picture isn’t necessarily wrong, it’s definitely incomplete. One of the largest reef systems in the world sits right off the islands, luring divers and anglers alike. Kiteboarders have ideal conditions, and boaters can spend days exploring mangrove mazes and uninhabited islands. To uncover the best adventures from Key Largo to Key West, we asked some of the islands’ most colorful locals for their favorite outings. 

Go Diving and Help with Reef Restoration in Key Largo

Home to John Pennekamp Coral Reef State Park, the first underwater park in the U.S., and a smattering of other bucket-list-worthy dive sites, Key Largo is a hot spot for scuba divers. “The diving is wonderful for new divers and snorkelers in particular because it’s really shallow and easy to see everything,” says Roxane Boonstra, a marine biologist turned dive instructor who now works for the Key Largo–based Coral Restoration Foundation.

Boonstra’s work centers on rejuvenating the 250-mile-long Florida Reef, but it also offers visitors a unique opportunity to participate. You can volunteer with the foundation at two sites off Key Largo, Carysfort Reef and Horseshoe Reef, for daylong dives where you’ll plant new corals grown by the organization in offshore nurseries, affording you the opportunity to explore one of the best dive sites in the country and leave it better than you found it. 

Learn to Spearfish in Islamorada

This cluster of six small islands south of Key Largo may be known as the Sport Fishing Capital of the World, but according to local Eric Billips, the most satisfying way to catch a fish in Islamorada is in the water. Billips owns Florida Keys Spearfishing Company and, in as few as two dives, teaches newbies this ancient craft that blends hunting, diving, and fishing. “When you catch a fish this way, you feel so much pride,” says Billips. “It’s the most sustainable way to harvest fish because you’re hunting one fish at a time.” 

Taking that environmental perspective a step further, Billips likes to target lionfish, a colorful but invasive (and tasty) species that has infiltrated the local waters during the last decade. The best part: “We fillet your fish up for you and you can take it to any restaurant in the area and they’ll cook your catch.” For cooking duties, Billips recommends Lazy Days, a laid-back fish camp on the water. “The decor hasn’t changed since the seventies, but that’s part of the beachy vibe.” 

Try All the Board Sports in Marathon

The 13 islands that make up the town of Marathon have become ground zero for learning wind and board sports, giving the normally languorous Keys a healthy infusion of adrenaline. 

“The Keys have all this potential besides just drinking cocktails and sitting on a porch and reading Hemingway,” says Matt Sexton, owner of Grassy Flats Eco Resort and Keys Cable Watersports Park, in Grassy Key, the easternmost island in the town of Marathon. Sexton’s park features an overhead cable system inside a five-acre saltwater lagoon to help new riders learn the nuances of wakeboarding and kiteboarding. 

Once you learn the basics in the lagoon, you can make your way out to the Florida Bay. Sexton says the bay’s shallow water (only waist deep for a mile in any direction) and consistent trade winds make it ideal for kiteboarders in particular. If there’s no wind, rent a paddleboard and head to the vibrant patch reefs in Hawk Channel. Bring a mask and fins—the snorkeling there is wonderful.

No matter how you spend your day on the water, Sexton recommends winding down at Herbie’s, a watering hole and restaurant inside an original conch-style building from the forties. “The owner refuses to buy any beer from big breweries—and he’s unapologetic about it. It’s a classic beer hall.”

Get Nautical in Big Pine Key & Florida's Lower Keys

Blanketed by Australian pines and home to the protected small Key deer, Big Pine Key might just be the wildest island in the chain. “There’s a lot of wilderness on Big Pine, but boating is the culture down here,” says Brian Branigan, author of The Road to Key West and owner of The Keys Boat Tours. Branigan offers lessons in both motorboats and sailboats that will get you comfortable driving and navigating the islands that surround Big Pine. 

Once you can drive a boat, the Keys become a whole new world waiting to be explored. For a short trip from Big Pine, Branigan recommends Looe Key, a tiny island four miles out in the Atlantic surrounded by its own National Marine Sanctuary with top-notch snorkeling. If you’re truly adventurous, Branigan can set you up with a sailboat and a fully loaded GPS (and emergency land and water support) that will guide you on a five-day cruise through the Keys backcountry, from Bahia Honda down to Key West, with detailed instructions on where to fish, where to snorkel, and where to anchor at night.

Back on dry land, head west through the lower keys to Stock Island and hit the Hogfish Bar and Grill for “dock to dish” seafood (get the hogfish sandwich on Cuban bread) in an atmosphere that still offers a glimpse of what the area was like in the sixties. 

Taste the Locals’ Key West 

Key West is known as much for its carefree nightlife as it is for its easy island vibe, but according to Analise Smith, who was born and raised on the island, all you have to do to avoid the crowds is wander off of Duval Street, Key West’s main drag. “Poke your head down any of the back alleys in Key West, and you’ll get a better sense of what the island is really about,” says Smith, who owns Key West Food Tours, a walking exploration of the city’s best restaurants and bars that gives visitors a taste of the Cuban and Caribbean cultures that influence the Keys. “Eating the local food is how you understand the culture. And the Keys have fish and fruit that you can’t get anywhere else in the United States.” 

Smith says everyone should seek out the Spanish lime, a sweet lychee-like fruit that locals go wild over, and porgy, a white fish that’s similar to grouper but a fraction of the price. Smith recommends hitting El Siboney, a Cuban restaurant that has been a staple in Key West for 50 years. “It’s in a residential neighborhood, and you'll feel like you’re in the wrong place, but the smell of onion and garlic lets you know you’re in the right place.” Order the roast pork, which Smith says is even better the second day. For cocktails, meander over to Mary Ellen’s, down a back alley off Duval, which is known in the neighborhood for its fun events, like the weekly (and well lubricated) spelling bee. 


With some of the world’s best fishing and diving, a thriving art and music scene, an incredible variety of restaurants and bars, and our legendary laid back attitude, the best part of a visit to The Florida Keys may just be tomorrow.

Lead Photo: Cody Spinadel