Picture of the Moorings Village Resort beachfront in the morning

Palm pilot: The Moorings Village resort is docked oceanside in Islamorada, Florida.

Photograph by Kris Davidson

By Elaine Glusac

Crab and lobster traps pile high in the parking lot of Keys Fisheries in Marathon, Florida, a wharf magnet for seafood lovers who crave a side of satire with their stone crabs. “Road Runner, your order’s up!” the loudspeaker booms, and the customer with the comic alias (one is required when you order) picks up his lobster Reuben. The underlying message? Don’t take life—or the Florida Keys—too seriously.

That refrain repeats over a hundred miles of some of America’s most improbably located blacktop. Skipping across dozens of islands and sailing over water, the running stitch that is southernmost U.S. 1—aka the Overseas Highway—bastes the Florida Keys to the mainland. Bankrolled by Standard Oil tycoon Henry Flagler, the route opened in 1912 as a railway linking the shipping port of southern Key West northward over steel tracks, riveted to coral and mangrove knobs and jumping over 42 ocean-footed spans (including the famous Seven Mile Bridge). Critics pegged the project “Flagler’s Folly,” and in 1935 a Category 5 hurricane proved them right. The engineering marvel toppled, adding the industrialist to the list of dreamers and dropouts whose legacy lives on here at this remote tip of Florida, from Blackbeard to Jimmy Buffett, Cuban exiles to “Conch Republic” separatists (in 1982 Key West declared itself a micro-nation in a tongue-in-cheek secession).

Beginning some 60 miles south of Miami, the drive from Key Largo to Key West showcases quirky islanders past and present as well as the archipelago’s natural assets. Atlantic-to-Gulf panoramas sprawl across islands often barely wider than the road. And alongside tacky souvenir stands and funky roadhouses are endangered herds of elfin Key deer, massive bird and wildlife sanctuaries, and the only living barrier coral reef in the continental U.S.

At the visitors center on Key Largo, greeter Jessica Lovejoy likes to joke that the gateway to the Keys is “seven miles of diving and drinking.” Yet even in this margarita mecca, it’s clear that diving comes first. The 2,900-square-nautical-mile Florida Keys National Marine Sanctuary, with its living coral and teeming fish life, acts as a buffer for the islands. An ideal spot to access it is John Pennekamp Coral Reef State Park, an offshore park that’s more ocean than land. Glass-bottom boat tours weave through mangrove canals en route to the reef where snorkelers plunge into a vibrant, textured wilderness of spongy anemones, stony corals such as star and brain corals, spiky sea urchins, and sinuous nurse sharks.

As you skim southward on the (mostly) two-lane highway, bridges leap over channels, manatee-shaped mailboxes picket driveways, seagulls race cars, and anglers cast off from decaying piers. Once part of the Over-Sea Railroad, those piers give sculptural testament to industry arrested by nature. Time and again in these parts, man and nature collude to make art out of the landscape. Bahia Honda State Park’s historic railroad bridge, now a pedestrian pier, strikes a dramatic pose as it juts nearly a mile into the water. Even beachcombers get in on the act, using Sandspur Beach as their canvas. “I call it Florida Christmas,” says one as he fishes a clamshell from the shallows to ornament a branch of one of the festooned sea grape trees lining the white-sand beach.

If the views haven’t driven you to ease your pedal pressure, the many speed traps along the route surely will. It’s more than ticket fines local police officers have in mind. On Big Pine Key, a motorcycle cop regularly idles with a sign broadcasting 150 Key deer roadkills last year, in spite of the efforts of National Key Deer Refuge to protect its dwarf-like namesake. At the end of Key Deer Boulevard, bucks with velvet antlers often emerge from the forest of saw palmettos and slash pines to graze on roadside grass. According to one park ranger, endemic Key deer “have no natural predators, other than speeding cars.” In other words: Slow down, and keep an eye out for the endangered creatures.

Beyond the Lower Keys lie more than 400,000 acres of water containing hundreds of remote islands protected by the Key West and Great White Heron National Wildlife Refuges. “The Lower Keys are just a door to the backcountry for a lot of locals,” says Victoria Impallomeni-Spencer of Dancing Dolphin Spirits Charters. That wilderness is where she steers the Imp II, her 25-foot powerboat, in search of dolphins, luring the graceful sea creatures with the violin music of Itzhak Perlman. On deserted islands in this “backcountry,” shells pile ankle-high on bleach-blond strands.

At mile marker 0, Key West is the island chain’s last outpost of civilization, with shipwright-built captain’s mansions alongside modest wooden shacks, backstopped by the Southernmost Point alleging the closest place on U.S. soil to Cuba, 90 miles away. Debauchery reigns on saloon-heavy Duval Street and in public perception, though plenty of islanders proclaim an art scene that thrives thanks to four live theaters, symphony performances, and storefronts such as Gallery on Greene, where the works of 37 local artists take turns on the walls.

That dynamic builds on cultural cachet left over from John James Audubon and Ernest Hemingway. In 1832, ornithologist Audubon visited what is now the Audubon House and Tropical Gardens to document American birds. The house features 30 of his first-edition illustrations, including the mango hummingbird and roseate spoonbill. And from 1931 to 1940, Papa famously straddled Key West’s party and arty sects, drafting For Whom the Bell Tolls at the 1851 Hemingway Home and Museum. Now the creaky mansion is inhabited by 45 mostly six-toed cats that descended from the writer’s polydactyl pet, Snowball. Docents point out highlights ranging from Hemingway’s “gallery of wives” to a lush garden of hibiscus and bougainvillea. “People like to get married here,” says guide Steve Trogner. “The fact that Hemingway was divorced three times doesn’t seem to matter.”

At sunset on the waterfront, Key West’s current cast of characters crowd Mallory Square for a nightly carnival of sword swallowers, unicyclists, and guitar strummers with parrots perched on their shoulders (because, well, why not?). Here the local mode of travel is a beach bicycle—the more broken down, the better. “I’m proud to say I’ve got a bike that goes slower than most people walk,” says islander Tony Falcone, co-founder of the Fantasy Fest, a Mardi Gras–style party that takes over town each fall. “It’s too hot to rush.”

Chicago writer Elaine Glusac has been diving and driving the Florida Keys for two decades.

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