Key West - A Walking Tour of Family History

Key West... For some, it's that place where they bought the Mile Marker 0 magnet for their car, or where the last halfway decent season of The Real World was staged. For others, it's where Hemingway wasted away at the local bar, long before Jimmy Buffet arrived and created a cult following out of lousy music. But for yours truly, Key West is an odd mixture of both a place that's completely foreign and, strangely enough, sort of like home.


That foreign feeling was evident the minute we stepped off the Brilliance of the Seas and into the sweltering subtropical November heat. At first glance, Key West feels like every other cheesy port found on a Caribbean cruise, with a number of tour operators and shops selling useless trinkets, along with the occasional dude literally walking around with a parrot on his shoulder. 
Never have understood the attraction here..

Some would argue that Key West actually is a foreign port of call, having (sort of) seceded from the Union to form the Conch Republic back in the early 1980s. It doesn't take long, however, for that Twilight Zone feeling to pass and for the Key West that I love to emerge in its place. The one that's filled with an endless supply of rich history... specifically, my own. 
I wonder how many of those 0s have been stolen over the years.

Although I can barely relate to Key West's margarita drinking, flip flop wearing, independence seeking ways, 1/4 of the blood in my veins is native "Conch." Long before Florida really seceded from the Union, my ancestors made their way to Key West for a variety of reasons. The cigar trade brought some to the island, while others were shipwrecked by pirates - yes, pirates - en route to Tampa and apparently just decided that Key West was close enough. 
I'd have stayed too...

Fast forward a couple of centuries, MJ and I found ourselves face to face with the matriarch of that Conch heritage while roaming Mallory Square. There we found a bronze bust of Elizabetha Knight - my great-great-great-great grandmother. I'm not entirely certain, but there may actually be one more "great" in there. What we do know, however, is that she didn't have the best of luck in the husband department. 

From Mallory Square we set off down Whitehead Street, which runs parallel to notorious Duval, and soon came across another famous piece of family history. The Banyan House is impossible to miss and a regular highlight for anyone that explores the city via the uber-tacky Conch Train. It also happens to be the birthplace and childhood home of my grandfather, as well as an enormous opportunity missed. You see, most visitors just gaze at the towering banyan tree and historic B&B and move on, but I linger a little longer, pondering what might have been an early retirement for everyone in my family.
Why oh why didn't we keep this?!?

A little further down Whitehead one will find the Hemingway House and a few of his famous cats, but our next stop is actually found directly across the street. The Key West Lighthouse was decommissioned by the Navy nearly 50 years ago, but the beacon still stands as a landmark in the heart of town. My great-great aunt and uncle once called the historic lighthouse and its adjacent quarters home, which definitely would have made them the coolest aunt and uncle ever if I had been around during that time.

All of this walking helped us to work up an appetite, and thankfully I knew just the place for a quick lunch nearby. El Siboney is something of a Key West institution, serving perhaps the most authentic Cuban food outside of Havana. I can remember coming here as a kid and going through roughly 4 baskets of their mouth-watering Cuban bread. Thankfully, not much has changed in 25 years, including my degree of bread consumption.

Back outside in the sauna, MJ and I made our way over to Duval Street, stopped in for a slice at the Key Lime Pie Company (Note: Don't believe the hype. Go to Kermit's instead) before arriving at the next stop on our makeshift tour. St. Paul's Episcopal Church has to be one of the most ironically located houses of worship in the world. Multiple generations of my family were married here and all of the doors entering the church bear a plaque in remembrance of once ancestor or another. And yet today, St. Paul's stands as a gleaming white edifice surrounded on all sides by the debauchery of the Duval Street area, no doubt casting a bit of shame on those stumbling by in the small hours of the morning.

Of course, no telling of our family history in Key West would be complete without a mention of the game of golf. It was here that my connection to the game was born, with my grandfather and great-grandfather both serving as head professional at Key West Country Club. When he wasn't at Augusta or running the country, President Eisenhower would join the two quite often for a few rounds of golf. Before his arrival, the President would famously call and inquire about the severity of the mosquitos. If they were bad, an Air Force jet would arrive soon thereafter, drenching the course with a layer of insecticide. An abuse of power? Maybe, but golf is just that important.
Pretty sure it didn't look like this during their day.
Photo Courtesy KWGC.

The final stop on our tour of Key West is, somewhat morbidly, the same for many of my ancestors. The Key West Cemetery is well known for its stacked grave sites, and many generations are at rest within the gates of our family plot. To stand beside the grave of my great-grandmother, remembering the countless games of gin rummy she purposely lost to me as a kid, with her great-grandmother just a few feet away, always feels just a little bit surreal. But there is simply no better place to grasp how deep our family history runs on this tiny island than by stepping inside that gate.

And yet, the story of that history has largely come to an end, with most of our family having moved on from Key West - literally and figuratively - leaving behind a legacy that's a source of pride for us all. But just as all politics is local, all history is personal. Key West remains a very special place filled with equally special memories. It was here that I caught lobster by hand with my grandfather, and proposed to MJ at sunrise some 20 years later. Perhaps one day I'll share those stories with an inquisitive niece or nephew, adding a few more chapters to their own story of Key West.

Enjoy Your Stay