Road Trips

Three Days in the
Florida Keys

Words By WildsamPhotography by Rose Marie Cromwell



1 Feb 2024

Reading Time

5 minutes

Lazy days on the water, cabana bar nights, and all of the key lime pie.

Just being able to reach the Keys is a wonder. Until the railroad came, in 1912, only swirls of aqua and indigo connected this chain of coral islets. Today, they’re linked by the 42 bridges of the Overseas Highway—and by a thread of whimsy that weaves through their culture and history. Feral roosters strut across rainbow-painted streets. Costumed revelers raise piña coladas in rowdy Key West bars. And a different kind of wild lives here too: tarpon jump, reefs bloom and royal poinciana trees light up in a cayenne- colored blaze. After the Calusa and Tequesta tribes came Bahamian wreckers, then Cuban anglers and cigar makers, each wave of newcomers indelibly shaping the Keys’ architecture, music and food. Artists and writers have nursed a swashbuckling lore that stretches back to tales of pirates and lost gold, but the real treasures here have never been measured in dollars or doubloons.

Tarpon feeding.
A trail at John Pennekamp Coral Reef State Park.

Day 1

When Highway 1 drops out of the Miami ’burbs and onto Key Largo, it’s a vibe shift, for sure. The only things bustling on the uppermost key, 30 miles long by just a couple wide, are the scuba and boat-repair shops. Head to John Pennekamp Coral Reef State Park, the country’s first underwater park, where tour boats ferry divers and snorkelers to Molasses Reef while great white egrets watch from the mangroves. Underwater, it’s a shock of sea fans, silvery sergeant majors and parrotfish flickering past the fire coral—even the occasional sea turtle.

Afterwards, Key Largo Fisheries Backyard Cafe has the island’s freshest catch—you can watch it come in as boats sway in the marina. Then toast the day at the legendary Caribbean Club, opened as a private fishing club in 1938 and made famous by Bogart and Bacall in 1948’s Key Largo. Key lime rum punch and sunset on the deck: a classic Keys moment.

A couple watches the sunset at Caribbean Club.

Day 2

In Islamorada, on Upper Matecumbe Key, start the day at Lorelei Restaurant, a locals’ hangout with luscious shrimp and grits and bargain Bloodies. Then rent a kayak at Robbie’s Marina for a paddle past shallow seagrass beds, Bahamian cushion stars and darting stingrays to the wrecker ghost town at Indian Key Historic State Park.

Down the road, in Marathon, a 40-year-old loggerhead named Rebel greets visitors to The Turtle Hospital, a hit with families. Guided tours check in with younger turtles on the mend from hurt flippers and other ailments caused by boat collisions, pollution and debris. To the west, at Bahia Honda State Park, the striking, abandoned rail bridge juxtaposes man’s short-lived creations with nature’s more enduring ones, while beneath, snorkelers search for spiny lobster and queen conch.

Drive on, cautiously, through the National Key Deer Refuge on Big Pine Key to the infamous brothel turned bar No Name Pub, a worthy stop for pizza and house-made key lime pie.

Robbie's Marina
Key lime pie at Key Largo Fisheries Backyard Cafe.
Nurse sharks at Key Largo Fisheries Backyard Cafe.

Day 3


The SIDEWALK POETRY PROJECT, initiated in honor of the late Shel Silverstein, etches Key West walkways with verse.

The TENNESSEE WILLIAMS MUSEUM has ephemera from the playwright’s decades-long Key West tenure. He’s said to have finished A Streetcar Named Desire at La Concha Hotel.

The KEY WEST MUSEUM OF ART & HISTORY displays Williams’ watercolors, artifacts from the railroad era and more.

They call Key West the Conch Republic and “the last resort,” a not-so-sleepy bohemia at mile marker zero. Conquistadors called it Cayo Hueso, or Bone Island, and Spanish and Caribbean influences abound. Grab a café con leche or Cuban sandwich at Five Brothers Grocery, an institution since 1978, or curry goat from family-run Pepper Pot Island Cafe.

Memorabilia fills the Hemingway House, the colonial villa where Papa spent the ’30s, as do many descendants of his six-toed cat. It’s a highlight of the Key West Literary Seminar’s 90-minute Old Town walking tour, along with Books & Books, the shop founded by 85-year-old YA phenom Judy Blume.

Come happy hour, raise a glass at Captain Tony’s Saloon with ghosts of such bygone regulars as Hemingway, Truman Capote, Hunter S. Thompson and Elizabeth Bishop. Then catch a band at the Green Parrot, one of the Keys’ oldest watering holes. On any given day,” one local says, it’s a dive bar or the cultural center of the universe.”

Live music at Caribbean Club.


Jennifer Justus, Sarah Thomas and Brad Bertelli contributed to this story.

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