A Place To Stand

A reflection on the history, character, and enduring mystique of Key West’s most storied home.

The wrought iron gate in the middle of the brick wall of the 900 block of Whitehead Street is one of those places history passes by on a daily basis. Celebrities seeking a photo opportunity, creatives desirous of new inspiration, locals hosting out of town friends seeking a glimpse at the soul of Key West, tourists adding check marks to their bucket list itinerary’s and the cat lovers who visit feline friends old and new, all find their way to the Home of Hemingway.

Each new entrant is instantly in awe as they step beyond the brick wall. The house, built closer to 200 years ago than today, exudes an architectural style clearly impacted by the decades of its existence, each inhabitant leaving their mark as we humans tend to do.

Unique in Key West as a structure built from the very coral rock it stands atop, the nearly 1 acre lawn stretching out in meandering paths, foliage enhanced by man, overhanging and popping up in its various manicured forms, a world unto itself unfolds. A small ticket booth which isn’t really there due to preservation laws keeping its wheels intact for potential movement that may never come is now as much a part of the grounds as the towering palms and heritage trees, contains a smiling face asking where you’re from and is this your first time to come. $19 please, the equivalent of a few drink specials offered on nearby Duval, and the opportunity to take a step into “somewhere” becomes yours.

My own first steps on these most historic grounds were in the early 2000’s. A trip to the Florida Keys to celebrate my recent engagement included a walk through the gate and up to the wooden doors. The many cats, always numbering in the several dozen, pouncing around or lazily napping were an interesting peek into what was being offered here. A tour guide reminiscent of a fishing guide and even smelling of old salt, offered tidbits of information about the structure and those who’ve lived here, the most famous of which having one of the most intriguing names in history, Hemingway.

Ernest Hemingway had been born elsewhere but Key West became a part of his soul. Key Westers in his day were quick to claim him as one of their own. Perhaps even an honorary conch for those in the know. The Depression era of the 1930’s had this far flung rock in a state of near bankruptcy and efforts to turn it into a tourist destination included maps with sites to see, places to eat, and famous residents' homes. Ernest probably preferred the town in its barely there hanging on state, an authenticity that had plagued the island with a patina of piracy and of pioneering charting its own colonial tale now romanticized and retold. He quickly bought up reclaimed bricks from the many streets being modernized with asphalt paving and as the bar room stories and family legends are told, he hired locals, possibly paid in rum, to stack into an imposing wall, with the hope of keeping the gawkers at least a few feet from the front door of his home. This effort only proved to provide a backdrop for entertainers and merchants seeking opportunity to turn public interest into profit there on the sidewalk in front. A tradition still honored today a few blocks west in Mallory Square with a wide variety of sideshows and acts providing for modern moments to gawk.

His second wife Pauline had a cosmopolitan outlook on life and was known for her editorials extolling the latest trends and her impact on the home at 907 Whitehead is still felt today in the form of her fabulous chandeliers adorning the ceilings of each room, favored over ceiling fans proving that even decades ago, fashion over comfort and function, reigned.

Visitors today place their footsteps on the same wood and tiled floors Ernest, Pauline and their boys did. Hosting countless guests, some at parties which Pauline was world famous for, made the grounds of the grand estate a most sought after invitation. No doubt drinks were drunk, stories were told, and Pauline’s own joy at having Ernest’s, “last red cent” set in the poolside stone elevated the vibes for soirees and petite fetes. Attendees of more recent parties and events hoping they too might leave with stories worth being retold.

Ernest’s Writing Studio, arguably the most authentically intact space on the grounds, a testament to his own dedication to preservation and those who’ve resided in the home, owned, or maintained it since, is a place unlike all others. A small room, originally built to store hay and the other items associated with life in the mid- 1800’s, became the sanctuary where a great deal of some of America’s most important written works would be created. The tales are still shared today of this great man’s routine of waking early and banging out his inner creative thoughts on a typewriter right there in that spot before the day or emotions could get too hot. Editing of course is an afterthought.

I have the privilege to serve in the capacity as an Events Coordinator here at The Hemingway Home. My own inner thoughts and efforts are fine-tuned and focused on cobbling together the wares of vendors, curating menus of both food and drink, and establishing the exact timeline for milestone moments to be enjoyed is my own little contribution to continuing to relish in the experiences so quickly turned into historic tome.

I like to think that Pauline must’ve had friends who stopped by to help support the hostess tasks ever present when entertaining is at hand. The household staff members focused on sweeping away the dirt and grime, polishing the metals and glass, delighting in the right mood the lights would cast, setting this piece of land apart from the world just outside the gate behind which it stands. Revelry amongst invited guests and friends then and now still one of the greatest ways a night might be spent.

Stories abound of the characters who contributed to Ernest’s great works and it’s our privilege, those of us who work at The Hemingway Home, to continue the preservation of history while making our own mark for future generations to contemplate, understand and contribute to their own paths of growth.

The 61 cats who currently call the historic grounds home know they are the masters of the universe and it is the true masters of the universe, great humans with all the opportunity in the world to shape, shift, and grow who often joke of coming back in a next life as one of the most visited felines on Earth in one of the most special places to create, ignore the comings and goings of the larger world, and be at peace in the knowledge that like Ernest, we need not ignore our fears in order to be brave, just to conquer them by not dwelling on amassing wealth but by loving and banishing thoughts of death until we no longer can. A long sentence I know but how else to say so much when I do not have a writer’s hand.

The Hemingway Home, located at 907 Whitehead Street in the Southernmost City of the Continental USA, Key West, FL is open daily from 9am-5pm, 365 days a year. Private tours and after hours experiences can be planned and expertly coordinated for those souls seeking something more. Pauline would approve of the opportunity to hang chandeliers and gather together family and friends. We will even gladly point out her pride and joy, that Denver penny, just ask a tour guide for the who, what, where and when.

I am finishing writing this in my office above Ernest’s old garage around 2am. I lack Ernest’s early morning discipline but I do the best I can. And while that first engagement may have lead me here that first time to stand, it was beyond my divorce that I was afforded the real opportunity to grow some as a man upon this unique piece of land. Plan a visit through the gate and beyond the outer wall of bricks on your next Southernmost trip. Remember, it might just be a place to some but to most it’s one of those magical and mysterious places in our land where greatness once called it home and those still striving towards great things can for a short time come to stand.



-Ralph “Ralphie” Segar Jr.
Events Coordinator
The Hemingway Home
Key West, FL

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A Look Back at 2025 in the World of Ernest Hemingway

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Hemingway’s Unbelievable Survival in the African Wilderness