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Ernest Hemingway Home and Museum, Key West, Florida.  Gorgeous Photo courtesy of Grammaticus Bramlington, licensed via Creative Commons.

A Drinking Town with a Writing Problem

January 15, 2015

Ernest Hemingway, Tennessee Williams, Robert Frost, Shel Silverstein, Jimmy Buffet… do you see a trend here?  At some point all of these writers lived in, or spent significant time in, Key West, Florida.  We’ve technically not been staying in Key West itself.  With a young child, it’s not practical (i.e., too expensive) to rent enough space in Key West proper, so we’re a few miles up the Overseas Highway in a very nice little house in the lower Florida Keys, on the water.     

There’s a reason people who like to write migrate down here.  The pace of life is much slower.  It’s easy to concentrate.  I’ve written more this week than I have in the past month.  I’m on vacation, but I’m actually inspired to work for a few hours each morning.  The one disappointment I have, and one that’s been echoed by some locals I’ve spoken with, is that there really is a "writing problem," as the town of Key West itself loses its flavor as a literary town and becomes more commercialized and corporate.  Key West always has been a tourist destination, but I’ve noticed a marked difference from even five or six years ago.  Many of the old standby “classic” Keys restaurants have taken on that “chain restaurant” feel and are now serving what is obviously frozen seafood.  Since 2011, three bookshops have closed, and a town with the literary tradition of Key West threatens to be left without a bookstore.  

But all that aside, there’s still a distinct “writerly” vibe here, Some things to do (besides write) if you ever get to spend time in one of my favorite places on earth: 

  • Drink.  This goes without saying.  There are approximately 400 places to buy alcohol in a two square mile radius.  
  • Visit the Ernest Hemingway Home and Museum.  Hemingway spent 10 years living and writing in Key West, from 1931 to 1940, when he moved to Cuba.  The house itself was built in 1851 and has a colorful history.    
  • Sloppy Joe’s Bar.  The bar that has made millions billing itself as the place where Hemingway drank.    
  • Captain Tony's Saloon (aka, “The Original Sloppy Joe’s,” 1933-1937.  The building allegedly is a former city morgue.) From what I can tell, the bar now called Captain Tony's is probably the place where Hemingway really drank (or at least the place where you’d like to envision Hemingway drinking).  There’s a great article here on an ongoing dispute between these two fine establishments, though knowing my own personal preferences, I'd probably have one hell of a night at Captain Tony’s, while at Sloppy Joe’s you might find yourself debating the merits of respective cruise line all-you-can-eat buffets with the guy on the next bar stool.)    
  • If you visit Key West in early January, attend the Key West Literary Seminar.  
  • Go fishing.  Boats advertising charters are everywhere.  
  • Read.  But soon you may have to bring your own books.  Shockingly, Key West Island Books is the last bookstore left in Key West.      
  • Just do nothing.  I've been doing a lot of this.  

And for those of you who will inevitably ask, no, there's not a pen store, but if I ever decide to hang up this lawyer gig, it's not out of the question.  

View From My Back Deck.
View From My Back Deck.

A little cloudy, but I'll take it. 

Captain Tony's Saloon
Captain Tony's Saloon

"The Original Sloppy Joe's"? 

Photo courtesy of Sam Howzit. Licensed via Creative Commons.

Sloppy Joe's Bar
Sloppy Joe's Bar

The "New" Sloppy Joe's Bar.  

Photo courtesy of Eric Kilby. Licensed via Creative Commons.

View From My Back Deck. Captain Tony's Saloon Sloppy Joe's Bar
In Travel Tags Key West, Travel
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