CHEECA #TBT: In the Beginning

Every week, social media’s #TBT brings us reminders of the people and places — and more importantly, hairstyles — that have defined our past.

But while you’re searching through old vacation photos to post on Facebook, it probably hasn’t occurred to you that your favorite vacation destination has a pretty interesting history of its own.

Allow us to share: While Cheeca prides itself on offering the finest in amenities and hospitality expected by the modern traveler, we also have a rich history as a landmark property in the Florida Keys. So we decided that we’d highlight some of our own favorite memories, famous visitors, and throwback photographs — to bring you closer than ever to Cheeca’s legacy. (But please, don’t judge our hair.)

Image by www,

It’s best to start at the start, of course. So this month’s #TBT takes us all the way back to 1919. What you’re looking at above is the Matecumbe Club — otherwise known as the “Millionaire’s Club” — an exclusive property that once stood right by the current Cheeca Lodge. You see, during the 1800s the Keys hardy early pioneers (known as the “Conchs”) constructed the very first buildings of Islamorada right on the beach where Cheeca is now. Among them was an old church and schoolhouse; there was even a small pioneer cemetery, now a designated historic site that Cheeca helps protect. (You can still visit it today.)

Today, the contemporary Florida Keys Overseas Highway follows the historic railroad's route through the Keys. Photo courtesy of the Monroe County Library

In 1905, the building of the Overseas Railway linked the Keys to Miami and beyond, and the islands slowly began to build their reputation as a sportsman’s paradise. (That literary legends like Ernest Hemingway waxed romantic about us didn’t exactly hurt.) In these earliest days of Keys tourism, a handful of 11 businessmen from the New York Cotton Exchange built the Matecumbe Club, designed as an exclusive and discreet getaway for the wealthy. One of its more prominent members was Lunsford Richardson and his brother Smith, who founded the Vick Chemical Company. The Richardsons would take a private rail car from their native Greensboro, North Carolina, all the way down to Flagler’s railroad, which took them on to the Islamorada Rail Station. (And you thought your flight was long?)

The Florida Keys Memorial is located next to Cheeca. Photo courtesy of US National Archives

The Matecumbe Club, like many of Islamorada’s most historic buildings, was destroyed in the infamous Labor Day Hurricane of 1935 — a Category 5 storm that is still considered the most intense hurricane to ever hit the US, based on atmospheric pressure. But its building marked an important moment in the island’s history: It was a spark that helped to fire up the Keys’ tourism reputation, one that has only grown stronger and more exciting over the years. (Not many of us can say that after looking at our #TBT photos!)

That’s just a quick glimpse at some of the fascinating history associated with Cheeca Lodge and Islamorada. Check back soon for another #TBT photo as we surf along the Cheeca timeline.

Have a #TBT photo of your own Cheeca getaway? Share it with us on Facebook, Instagram, and Twitter.

#CheecaTBT #SayCheeca

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