Three Days in the Florida Keys

Three Days in the Florida Keys

Three Days in the Florida Keys

Our quick guide to getting tropical.

A different wild lives out in the Florida Keys than at the bars of Duval Street, where the piña coladas and margaritas whirl. A vibrancy unfolds quietly, all the time. Beneath the water’s surface, where the tarpon swim, divers float amid the coral reef with its shock of colors, hunting shipwrecks and their stories. Along the backstreets and alleys, lizards skitter. Royal poinciana trees light up in a cayenne-colored blaze. 

Just being here is a wonder. Before the railroad or highways, only aqua and indigo connected this jangle of tiny islands. Today: 42 bridges, about 45 miles per hour. It remains a commitment to come here, and to be here. Despite–or maybe because of–those challenges, whimsy weaves through the place.

The deeper story embraces Calusa and Tequesta tribes living on the water’s bounty, Cuban fishermen, cigar makers, Bahamian wreckers, whose cultures carry on in music and architecture. Generations of families keep their histories alive through the cafés con leche and Cuban sandwiches passed across countertops. The legends stretch and twist back to tales of pirates and lost gold, but the real treasures here have never been monetary.

Here’s a peek at our island intel, including the best spots to take in the Keys’ natural beauty, roadside diners and literary history.


Day One

You’ll take the Overseas Highway, naturally. A dream drive over the unlikeliest terrain–a spray of keys amid the swirl of blue and green waters, threaded together by 42 bridges.

First stop, Key Largo. 

When Highway 1 drops into this uppermost Key, it’s a vibe shift for sure. The Keys’ largest island stretches 30 miles long by a couple miles wide, dotted with sea culture on every corner, scuba centers to boat repair shops and conservation too, with organizations like the Coral Restoration Foundation. And in the Dive Capital of the World, John Pennekamp Coral Reef State Park is an explorer’s hub. 

But first, a bite at Mrs. Mac’s Kitchen, a roadside favorite (fish and grits!) since 1976. Look for the pink cottage with gingerbread trim in Bahamian architectural style. And remember, it’s never too early for key lime pie. 

Dive in afterward at Pennekamp, a great first taste of the Florida Keys National Marine Sanctuary, which stretches the length of the Keys (and beyond), with nearly 3,000 square nautical miles of coastal and oceanic ecosystem teeming with fish, coral, birds. Protected but free. Precarious yet wild and mysterious.

Snorkeling and diving obviously provide the best viewing of the reef. Otherwise, the glass-bottom boat tours can be thrilling, thanks in part to the excellent park guides. As the ferry slow-rolls through mangroves, they offer bird-watching lessons while great white egrets stand watch. When the boat reaches Molasses Reef, the guides take on the speed and urgency of auctioneers, calling out fish and reef formations as they see them–hogfish, sea fans, fire coral, black grouper, parrotfish, sergeant majors, nurse shark, sea turtle! Other head-above-water pursuits: kayak or paddleboard rental for exploring 50 miles of mangroves, or hikes along trails through hardwood hammock. 


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To sample the best of the edible ocean, curl behind Key Largo Civic Center to Key Largo Fisheries, a marina with a menu board stacked with hogfish, snapper and mahi. Watch fishermen come in with their catch amid the sways and squeaks of boats against buoys. 

Toast the day with a sunset drink at Caribbean Club, one of the oldest and greatest roadside attractions in the Florida Keys. What began as a private fishing club built by Carl Fisher in 1938 grew into much more, thanks in part to the Humphrey Bogart and Lauren Bacall classic Key Largo, released 10 years later. The film was shot on a California set, but the screenplay was written at the Caribbean Club during a stay by director John Huston and screenwriter Richard Brooks. 

The low-slung Caribbean Club continues to stir up key lime rum punch, and a view of the sinking sun here remains a classic Keys moment. 


Day Two

With water all around, the Upper to Lower Keys don’t sit on much land mass, but they do provide vast options for exploration. A choose-your-own-adventure day offers much to see along the stretch between Key Largo and Key West. 

To start, look for the mermaid at Mile Marker 82 in Islamorada. She signals breakfast at the Lorelei Restaurant & Cabana Bar. Over shrimp and grits or burritos, gaze across Florida Bay, where green mangrove break up the blues. Once caffeinated, head for Robbie’s Marina. When the marina’s namesake found an injured tarpon in the 1980s, he called a local doctor, who brought his wife’s upholstery needle to the dock and sewed the fish’s jaw together. Robbie released “Scarface” the tarpon, but he only swam far enough to invite his friends. The silver kings have orbited the dock ever since.

At Robbie’s, The Kayak Shack can provide a rental. Paddling out to Indian Key Historic State Park takes about 30 minutes, crossing shallow seagrass beds where small sharks and stingrays sometimes dart away. Puffy, orange Bahamian cushion stars can be seen in the seagrass meadow too. A community of wreckers lived on Indian Key’s 11 acres in the 1830s, keeping a watchful eye for ships run aground. Acting as first responders–sort of–they rescued crews and salvaged cargo. The first to arrive at the scene would be named wreck master, usually getting around 25 percent of the cargo’s value. By 1835, Indian Key had a restaurant, hotel and nine-pin bowling alley. It’s a ghost town today, with paths for exploring village ruins. 

After snorkeling around the island, paddle back for a well-earned Iguana Bait Kölsch at Florida Keys Brewing Company with a bite from Tacos Jalisco, the truck parked out by the brewery’s beer garden, where brightly colored picnic tables turn magical under twinkling lights hung from tropical flowering trees. Or visit one of the vintage roadside spots, which popped up after the Overseas Railway became the Overseas Highway. A neon sign beckons travelers to The Green Turtle, which has been serving fish dishes and tall tales in this Sports Fishing Capital of the World since 1947. 

Continuing on to Marathon, human visitors can learn about harm to turtles through pollution, debris and boat collisions at The Turtle Hospital. You might meet a 40-year-old loggerhead named Rebel, as well as younger turtles in recuperation pools for hurt flippers or other ailments. Thanks to the care here, some will swim in ocean waters again. 

Indeed, the 30-minute trip from Marathon to Big Pine in the Lower Keys–including about 10 minutes crossing the Seven Mile Bridge–can be a marvel, an enlightenment, a beauty, and a reminder of our fragile world and the reasons to tread lightly. A splendid spot to take in the natural beauty of the Keys: Bahia Honda State Park. Snorkelers float over seagrass and search for spiny lobster and queen conch. Boats venture farther to Looe Key for snorkeling or diving the protected Looe Key Reef. The old rail bridge at the park juxtaposes man’s efforts with enduring nature. (Camping and stellar stargazing can happen here too.)

If traveling on, drive cautiously between Bahia Honda (Mile Marker 36) and Sugarloaf Key (Mile Marker 16), especially in early morning or late afternoon when key deer sometimes wander near the highway to nibble on grasses. The crossing signs in the area will alert you to the area’s endangered species. The smallest white-tailed deer subspecies measures around just 32 inches tall at the shoulder–about the size of a large dog–with bucks weighing 55-75 pounds. 

As early as 1575, Spanish shipwreck survivor Hernando de Escalante Fontaneda wrote about key deer. By the 1940s, fewer than 50 remained. The establishment of the National Key Deer Refuge in 1957 helped the little deer turn a corner, and today their population has risen to about 750. They swim between 25 or so islands in the Lower Keys for food and water but mostly congregate on Big Pine and No Name keys. The refuge has several trails, such as the Watson, a ⅔-mile loop. But resist the urge to feed any deer you encounter. They have been conditioned to find gardens and trash cans, which brings them closer to neighborhoods and roadways, where they become more susceptible to dog attacks and traffic accidents. 

Finish the day at Square Grouper Bar and Grill in Cudjoe Key. With a corrugated-metal warehouse aesthetic, it doesn’t look like much on the outside. But like the location in Islamorada (should you not make it as far as Cudjoe), the restaurant draws loyal locals for dishes like roast duck with tamarind garlic sauce and almond-encrusted grouper with pineapple relish.




Day Three

They call Key West the “last resort”–the not-so-sleepy bohemia at Mile Marker Zero of Highway 1. The Spanish took to calling the place Cayo Hueso, or “Bone Island,” and Spanish and Caribbean influences echo in architecture and attitude. Pick up a Cuban café con leche from the walk-up window at Sandy’s Cafe and venture on to breakfast with the roosters at Blue Heaven, known for lobster Benedict and warm banana bread. 

Then for a wander through the exceptional literary heritage of Key West, begin at The Hemingway House, where Ernest Hemingway wrote and lived in the 1930s with second wife Pauline Pfeiffer. Highlights: the writing studio, the poolside excerpt by Elizabeth Bishop and the many adorable polydactyl [six-toed] cats that still roam the grounds, some thought to be descended from Papa H.’s own cat, Snow White. 

Pop into Moondog Cafe on your way downtown for lunch or pastries in a space beautified by local artists and many a present-day working writer curled over a laptop. Look down as you walk–the Sidewalk Poetry Project, initiated in honor of late Key West poet Shel Silverstein, populates the city sidewalks with verses. Stop off at Books & Books, YA phenomenon Judy Blume’s neighborhood bookstore, featuring a robust section of writers who have called this island town home, and is attached to The Studios of Key West, which hosts ever-rotating art exhibits. 

Then, amble to the hibiscus-pink Monroe County Public Library to visit the staff historian in the Florida History Room, a treasure chest of maps, historic letters and literary artifacts, and find a shady spot in the courtyard to read. A visit to the Tennessee Williams Museum provides insight into the celebrated playwright’s life here, from 1941 until his death in 1983; he is said to have finished A Streetcar Named Desire while staying at LaConcha Hotel on Duval Street. Visitors can also see his watercolors at The Key West Museum of Art & History. 

For those who want the master class in Key West writers, visit during the Key West Literary Seminar in January. The nonprofit purchased the former home of celebrated poet Elizabeth Bishop in 2019, which will serve as a headquarters and public resource. To see all the sites, take KWLS’s Old Town Literary Walking Tour.

To finish the day, raise a glass of something cold at Captain Tony’s Saloon, the original “Sloppy Joe’s,” where not only Hemingway but also Truman Capote and Hunter S. Thompson are said to have imbibed. (Famous patrons’ names adorn the barstools. Unknown patrons’ bras adorn the ceiling.) 

Come evening, it’s mojitos and ceviche at El Meson de Pepe and live shows at the Green Parrot. Says one local of the beloved bar: “Any given day, it’s a dive bar, or the cultural center of the universe.”


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Find more itineraries in Wildsam’s Florida Keys, including recs for restaurants, shops, bars, hotels; interviews with anglers, writers, maritime archaeologists, Cuban grocers; a deep-water look into dive culture; and essays on fishing and shipwreck exploration.