Overnights on the Overseas Highway: A 113 Mile Journey Discovering Florida’s Most Storied Hotels

No less than 42 bridges slice through scattered coral and limestone islands, sand spits, mangroves and cays harboring wildlife refuges, marine sanctuaries and protected ecosystems linking Key West to the mainland along the Overseas Highway. Waters of the Atlantic Ocean and Gulf of Mexico shift from deep emerald to shimmering azure on either side, splattered with swooping pelicans, cormorants, great white herons and a never-ending parade of lobster, crab, and deep-sea fishing boats.

You can’t cross the sea merely by standing and staring at the water

Rabindranath Tagore

As I turn onto the simulated gangplank stretching for 113 miles toward the southernmost tip of America, hundreds of small islets string like colorful tails on a dancing kite. It was tempting to just pop the ragtop and fly like the wind all the way to Key West, home to some of Florida’s most intriguing historic hotels. But instinct tells me there are plenty of stories lurking between every milepost along the Overseas Highway, ones with plots and characters unlike anywhere else in the world.

From the Key Largo of ‘Bogey and Bacall’ to Islamorada where the Rayburn family took viewers deep into the underbelly of the Florida Keys in the noir thriller series “Bloodline,” the world’s fascination with this storied strip of highway is more than justified.

Hold Your Course

Mile Marker 106 in Key Largo epitomizes 1940s lore of the Florida Keys, where travelers expect to roam through storied Florida Keys hotels, like the shambolic Hotel Largo where Humphrey Bogart and Lauren Bacall “had it all.” The 1948 film and 1982 song forever immortalized Key Largo as the ultimate romantic destination in the Keys, but in reality, the Florida Keys hotel never actually existed.

“Hold your course. You’re headed straight for Key Largo…”

‘Key Largo’ with Humphrey Bogart, 1948

That doesn’t stop me from taking a tumble through history at the 1938 Caribbean Club that inspired the fictional Key Largo hotel where scenes from the iconic “Key Largo” movie were shot. The oldest bar in the Upper Keys still exists there and also served as the watering hole where characters from “Bloodline” drank away their sorrows or devised sinister cover-ups. The tatty lounge swirls up swarthy rum-runner cocktails and live music at sunset as it’s done for decades.

Never mind that tales of actual rum runners, rogue pirates, native massacres and sunken ships abound in the Florida Keys. But ironically, in the midst of bones, burials and bombarded vessels, the only living coral barrier reef in the United States flourishes like an aquatic Garden of Eden, virgin and untouched.

Pennekamp Coral Reef State Park harbors at least 40 species of coral and 500 varieties of exotic sea creatures – not to mention the unsettling two-ton submerged bronze ‘Christ of the Abyss’ statue lurking in the depths with outstretched arms. About six nautical miles off the coast of Key Largo, Carysfort Coral Reef occupies the southernmost tip of the Bermuda Triangle where ships and aircraft still mysteriously disappear into oblivion.

20,000 Leagues Under the Sea

Divers and snorkelers are cautioned before entering the reef zone that any contact with human touch will cause the reef to perish, each tiny tainted coral contributing to an eventual devastation in the depths. Nobody touches. But they do go down there, and some even sleep on the ocean floor, about 30 feet below the surface of Emerald Lagoon.

Named for Jules Vern, author of “20,000 Leagues Under the Sea,” Jule’s Undersea Lodge is far from a fabricated sea gimmick. For years, this Florida Keys hotel served as the La Chulpa Research Laboratory, a marine lab off the coast of Puerto Rico. It’s one of the only hotels in America whose dress code includes mandatory scuba gear and the lobby begins at 21 feet down-under. The two-bedroom 1-bath suite includes food delivery and is encapsulated within 42-inch round windows for ultimate ogling at sea creatures (and vice versa) in the dead of night.

Checking into this Florida Keys hotel requires scuba certification and diving through an underwater tropical mangrove habitat. It just so happens that they run a Discover SCUBA Diving course in the lagoon, so there’s no excuse for avoiding the overnight plunge. I wonder how many underwater guests stay up all night watching “Jaws” or “Tentacles of the Deep” on the provided Amazon Fire TV Stick. Jules Undersea Lodge has itself served as a set location for everything from “Good Morning America,” to the Food Channel, the BBC, and the Playboy Channel.

Before leaving Key Largo toward Islamorada, I make one more stop in homage to nostalgic films. Mile Marker 100 cradles the African Queen boat (aka the S/L Livingstone) that once operated in the Ruki River of the Congo and later starred in the 1951 “African Queen” movie starring Humphrey Bogart and Katharine Hepburn.

A Village of Islands

Islamorada, contrary to its often-mispronounced name, has nothing to do with Islam. In fact, you’d be hard-pressed to find anything remotely resembling religion in this “village of islands” where sports fishing has god-like status. From marlin to mahi-mahi, sailfish, amberjack, wahoo and tarpon, these are the apostles of the Keys, and reeling in the elusive gray ghost bonefish is the ultimate angler ascension. The tall-tales of Islamorada spring from hundreds of seafaring vessels engaged in night fishing, lobster diving, stone crabbing, wreck and reef fishing, and backcountry trawling in the Everglades.

This village of five islands is also the nascence of the dark and fictional (but highly believable) Rayburn family of the Netflix hit series “Bloodline” starring Sissy Spacek and Kyle Chandler. Unlike the fabricated setting for Hotel Largo, this one is as genuine as it gets.

The series was filmed entirely in the Florida Keys, and the iconic Rayburn House family inn is a real Florida Keys hotel that’s been welcoming guests for decades. Spreading its infamy across 18 acres and 18 cottages on the beach of a former coconut plantation, the Moorings Village and Spa personifies the complicated lifestyle of the Keys.

Genteel and gracious plantation families harbor generations-old secrets as deep as the murky mangrove swamps and as turbulent as the ocean that pushes and pulls in the dead of night, whipping into ferocious hurricanes that destroy everything in their paths. The Moorings itself was closed for months after Hurricane Irma crashed through Islamorada in 2017.

As “Bloodline” co-creator Todd Kessler put it when explaining to Hitfix why he chose the Florida Keys as the setting for his disturbingly dark story of the Rayburns:

“There is no place quite like the Keys … the color of the water and being outside and it really feeling like paradise … but then having this kind of underbelly of what’s going on underneath it.”

As if it’s impossible to unwrap the mystique of a place like Islamorada, Kessler states it simply:Something weird goes on down there.” Indeed it does. But you’d never know it on a lively night at the inn’s Morada Bay Beach Café.

I happened to arrive during a full moon when the beach at the Moorings suddenly bursts to life in a frenzy of Caribbean-style live music accompanied by acrobats, fire breathers, dancers, bonfires and fireworks exploding over the water. At the monthly full-moon parties, sizzling plates of yellowtail and stone crab appear along with key-lime mojitos and lavish seafood spreads, revealing a festive flip-side to the murky tales of “Bloodline.”

Hours later, I creaked methodically in the wooden rocking chair on my cottage veranda at the Moorings and locked eyes with an enormous iguana shimmering with startlingly vivid vermillion scales. I knew right then that I could either turn away or make peace with the yin-yang of these exquisitely intoxicating and multistoried islands. I did hide from the iguana ­– but I also hit the Overseas Highway at sunrise, heading to Key West.

Cayo Hueso, City of Bones

Cayo Hueso, the Spanish word for Key West, translates as “city of bones.” I quickly got the feeling that every night on this island is haunted in one way or another. But the days are thick and sweet, with scented mango blossoms hanging heavily in the humid air, cascading from the white-fenced balconies and verandas of literary giants like Ernest Hemingway and Tennessee Williams.

Here at the end of the Overseas Highway, with Cuba insight, if you squint your eyes and imagine Hemingway steering his beloved boat Pillar like a waterborne casket for 90 miles to fritter away his days in Havana, the protocol is murky at best. Dangling from the southernmost tip of the continental United States seems to have removed Key West from the usual proprietary obligations of social etiquette. In other words, inhibitions are best left on the mainland.

Shipwrecks and Slave Ships

The mysterious little conch cottages with clapboard siding and open porches in the Old Town of Key West hold 19th-century secrets of boat builders from the Bahamas slipping into the bay and erecting new lives in the watery tip of America. More than a few of these new immigrants likely floated unknowingly over shipwrecks and sunken treasure clinging to the past in watery graves.

Today, divers clad in high-tech gear slip in and out of these wrecks as though they were on a movie set. Ten-Fathom LedgeNine Foot Stake … the sites of these colossal failures mimic Hollywood blockbuster titles and pull adventurous souls into the ocean’s belly to swim with barracuda, spotted morays, horse-eye jacks, yellowtail snapper, eagle rays, hogfish, fire coral, elkhorn and myriad more with names that belie a civilization with its own order and purpose.

The name Cayo Hueso was coined by early Spanish explorers when they happened upon the skeletal remains of Native Americans while traversing this tiny bump of land. I guess it was to be expected at the tip of an island chain ending in nothing but water. Higgs Beach on the southern shore of the island cradles another travesty of bones, those belonging to captured West Africans rescued from slave ships in 1860 by the US Navy and brought ashore.

At least 295 of the 1,492 future slaves onboard the Wildfire, the William and the Bogota vessels never made it to their destination in Cuba or back to their homes in what are now the African countries of Benin and Congo. Dying from illness after the six-week treacherous journey, they apparently lived just 85 days on the southernmost tip of America

Most of their bones laid encrusted in sandy graves until relocated in 1862 while building towers to fortify the island during the dark days of the nation’s Civil War. Ground-penetrating radar data collected almost 150 years later revealed at least 100 sets of bones at Higgs Beach, some in tidy lines of 5- to 6-foot-long ovals a mere 2 to 3 feet beneath the surface.

The cemetery has now been consecrated and marked by pedestals inscribed with African Adinkra symbols, tile murals and a rendition of the perilous maritime slave route. It has more than earned its spot on the National Register of Historic Places.

The Conch Republic

For several weeks in Key West, I’d be historic-hotel hopping within a collection of six Historic Key West Hotels and Inns that look as though they were color-washed onto a throwback canvas of Old Florida in the late 1800s. There’s a reason for that: these Florida Keys hotels have been converted from former cigar magnate estates and small conch cottages, many housing tobacco workers from the Bahamas, Cuba and Haiti. Long before Key West was on the radar of anyone but pirates, natives and military captains, cigar factories made Key West one of the wealthiest enclaves of Florida, cranking out more than 60 million cigars every year.

I checked into Lighthouse Court on Whitehouse Street in time for the evening tradition of poolside cocktails at the inn’s mojito bar. Scents of citrus and lime claimed the evening air at this Florida Keys hotel, and an intoxicating sea breeze wafted inland, passing the historic Key West Lighthouse just behind us. I hadn’t realized yet that I was within spitting distance of Ernest Hemingway’s house and that I’d be laying my head that night in the lavish Hemingway Suite overlooking his sparsely decorated writing room and storied swimming pool.

The forty rooms and suites of Lighthouse Court spread across 10 conch buildings from 1890 through the 1920s, creating its own little village of sorts. The 1,000-square-foot Hemingway Suite feels enormous, and I rambled through the various rooms at this Florida Keys hotel before choosing (of course) to sleep in the master bed with a direct view of Hemingway’s front door.

In the early-morning sun, African tulips perching on Hemingway’s tree branches glistened with raindrops, the crimson petals forever straining toward the sky as if seeking their roots in the land that inspired some of the author’s most acclaimed works: Green Hills of Africa, The Snows of Kilimanjaro. Here in Key West, crows feast on the nectar of a thousand young blossoms that return year after year.

I walked across the street and introduced myself to the 50 or so polydactyl cats roaming the grounds of the estate, many of them descendants of Hemingway’s white six-toed cat named Snow White. I smile at the embedded penny in the pool’s courthouse memorializing the story of when he blamed his wife Pauline for spending his last penny building the pool while he was traveling as a war correspondent during the Spanish Civil War.

Cypress House and Breakfast With the Papas

If it seems that Hemingway’s memory occupies this island is hauntingly vivid ways, that’s because it really does. It’s not just the fact that he chose to build a home and raise his boys here – he actually inhabited Key West in the deepest sense of the word.

That’s why it was a bit unsettling when, after checking into the Cypress House Hotel, I came down for poolside breakfast and found myself dining with dozens of men stroking grey beards and looking exactly like “Papa” Hemingway in his older years.

As it turns out, Cypress House is a gathering spot for competitors in the annual Hemingway Look-a-Like contest. In a hotel with more than 100 years of history in Key West, I suppose mutating Hemingways are par for the course. Built in the late 1800s after a devastating fire destroyed much of Key West’s old-town enclave, the Cypress House was the estate home of avid naturalist and fisherman Richard Kemp who migrated to the Keys from the Bahamas.

The three conch-style buildings of the Florida Keys hotel retain the original unpainted cypress and pine cladding, along with eyebrow-style windows and classic-revival columns. It’s considered one of the most authentic examples of tropical-colonial architecture in Key West. It seems fitting that the lush Caribbean-style gardens of Cypress House host a “liming” ceremony every evening in which “the art of doing nothing” involves the sharing of food, stories, and laughter. If a panoply of Papas makes an appearance, we’re all the better for it.

Sea Swept

It would be almost a month before I turned in my cruiser bike and bikini and made the reverse journey across the Overseas Highway back to the mainland. Since I left, Hurricane Irma wreaked havoc on the islands and villages I’d come to both love and fear in inexplicable ways. But the rebirth of the storied Florida Keys hotels, inns and villas up and down the Keys mean a whole new slate of stories just waiting to be written, etched in time and swept by the sea.

“The sea is everything. It covers seven-tenths of the terrestrial globe. Its breath is pure and life-giving. It is an immense desert place where man is never lonely, for he senses the weaving of creation on every hand.”

Jules Vern, “20,000 Leagues Under the Sea”

More Stories
The Algonquin Hotel New York: Literary Legends Know Why The Caged Bird Sings