When you’ve planned a vacation to Key West, sometimes it seems like all you can do in the days leading up to it is to sit at your cubicle and dream of hitting the white sand before you lose yourself in the blue water.

While this famous Florida key has great beaches and is a fantastic place to unwind, there is more to the island of bones than just the sand and surf. If you want to get the most out of your vacation, you need to experience more than the fantastic beaches (but, by all means, pencil that in, too)!


For History Geeks: The Bone Key

Key West really is an island of bones or was at any rate. The name “Key West” is really just an Anglicized version of “cayo Hueso,” which is what the Spaniards called the island when they arrived to find the island piled high with the bones of the native dead. Literally translated it means “bone cay,” and was the communal graveyard. But, the island was the westernmost source of reliable water, so the creepy factor was ignored.

The key still maintains a cemetery worth looking at, and not just if you’re interested in gravesites as a hobby. These graves are absolutely beautiful and unique—it’s not every grave that is topped with a red airplane or has a painted tile portrait of the grave occupant, all alongside the European-style graves of dead Conchs—so they’re a site to see even if you’re not usually into hanging around cemeteries. If you are, so much the better!

The United States Military also has an interesting history on the Bone Key. Fort Taylor is an exciting example of Pre-Civil-War military architecture and artifacts—the fort, which held John Wilkes Booth’s Doctor Samuel A. Mudd for his life-in-prison sentence, still has most of its masonry and cannons intact. Also of military and historic significance is the Truman Annex neighborhood, a military housing development turned luxurious condo neighborhood. Truman’s “Little White House” is open for tours to paying guests.

More recent history (and a souvenir opportunity) includes the legacy of Key West’s “secession” from the United States and the formation of The Conch Republic. When the US Border Patrol set up a blockade that negatively impacted Key West’s vital tourist trade, the city council tried legal means but eventually declared their independence and took the name of the Conch Republic. It was more of a publicity stunt than a true secession, but it worked then and continues to do so; what then brought necessary media attention to the Federal Government accidentally ruining their major industry now brings Key West tourists and souvenir sales. You can buy Conch Republic flags and memorabilia at most major gift shops, and even purchase a Conch Republic Passport.

For Foodies: Conch Republic Cuisine 

Be sure to sample the best and most iconic foodstuffs of Key West in order to maximize your cultural experience.

Whether you’re eating out or getting something to eat on the deck of your vacation rental, there are a few things you must try.


  • Cuban Sandwiches: A Cuban sandwich is an iconic South Floridian foodstuff, mostly because of the large Cuban population. While the Cuban bread it is always made with is almost unmistakably a Tampa creation—a baguette-like creation that is unique among baguettes in its use of lard—the honor of the Cuban sandwich’s hometown is claimed by both Key West and Tampa. The Cuban sandwich consists of mustard, pickles, Swiss cheese, ham, roast pork, and sometimes salami on fresh Cuban bread. Then the sandwich is pressed on a special hot iron called a plancha until the cheese melts and the bread is crispy.
  • Key Lime Pie: This delicious and internationally enjoyed pie was almost certainly created in Key West. Wealthy ship salvager William Curry—the island’s first millionaire, his house is now a museum—claimed that the pie was made for him by his cook, Aunt Sally. The key lime juice came from the limes naturalized throughout the keys, and the sweetened condensed milk from a time before refrigeration was available. A true Conch key lime pie will use the whites leftover from the egg yolks in the pie filling to create a fluffy meringue topping. Many Key West vacation rentals have kitchens, so you can make key lime pie with key limes from Key West while you are in fact in Key West. Or you can buy it dipped in chocolate on a stick from an iconic shop on Duval Street.
  • Sloppy Joe’s: Not the sandwich; the bar & grill. Its original location, frequented by Hemingway and other Key West writers, is now Captain Tony’s Saloon. However, Sloppy Joe’s is the scene of live bands and the Ernest Hemingway look-alike contest, so if you like historic bars, visit both Joe’s and Captain Tony’s.


For Literature Fiends: Hemingway and Friends

Okay, it’s no secret that, if you love good literature, Key West conjures up images of Ernest Hemingway and his home. This home was the place where Hemingway wrote “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.”

The house is now a museum where you can see Hemingway’s reaction to a bill when he returned from working as a war correspondent; Hemingway reportedly threw the penny into his new pool saying “here, have my last cent.” Yes, it’s the same penny. Also at his house are the descendants of his famous polydactyl (extra-toed) cats, for which the house carries on a selective breeding program.

Although Tennessee Williams lived in Key West, that house is privately owned. You can still wander around to see the scenery from the Academy-award-winning film version of his play The Rose Tattoo, which was filmed on the island.

You may also want to stay on the island for the Key West Literary Seminar, which has attracted writers such as Joyce Carol Oates, Billy Collins, Margaret Atwood, and Annie Dillard, among many more.

There are hundreds ofthings to do in Key West, so whatever you choose to round out your beach time, you’re guaranteed an excellent adventure!

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