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Finding The Best Cuban Sandwich in Key West

You’ve heard it before. A surefire way to bring about discord in an otherwise informal public gathering is to bring up the taboo subjects of politics and religion. If you happen to casually mention something not so flattering about a trendy political topic while you’re sitting next to Uncle Bill at Thanksgiving dinner, don’t be surprised if the holiday spirit suddenly gets sucked right out of the room.

When it comes to food, there are plenty of sacred cows that you just don’t mess with either; and I’m not talking about burgers… There are those who insist that no place on earth produces better bagels or a better slice of pizza than New York City (I would bet there are a few Italians from Naples that would beg to differ with the latter.) If you want an authentic cheesesteak, head to the corner of 9th Street and Passyunk Ave. in Philadelphia and make the life-changing, controversial decision of either grabbing one at Geno’s or Pat’s. If you’re seen putting ketchup on a hot dog anywhere in the Greater Chicago area, you run the risk of winding up in the back of a police car.

The Cuban sandwich… that delectable, crunchy and savory gift from the sandwich gods, is also the subject of many a heated debate. There are as many histories as there are layers of flavor in this sandwich on how it found its way into the hearts and the restaurants of American life. Of no surprise at all is the fact that the Cuban sandwich has reached its near mythic status in the State of Florida, specifically Tampa, Miami and Key West.

close up of cuban sandwich and plantain chips

Tampa, for example, has claimed it as its own, attributing its beginnings as a snack the cigar plantation workers ate in Ybor City in the late 19th century. According to lore, the confluence of Spanish, Italian, Cuban, German and Jewish culinary traditions conspired to create the delectable masterpiece we know and love today, which includes the addition of salami. But if you talk to the average Miamian enjoying a thimble sized cup of the strong, local brew, they would scoff at the thought of putting salami on a Cuban sandwich.

What was this sandwich like in the place of its birth?

It was certainly not designated a ‘Cuban’ sandwich anymore than a piece of grilled meat between two pieces of bread you’d eat at the Texas State Fair would be called an “American Burger.” It is said that the sandwich has enjoyed a place at the Cuban table for over 400 years. The Spanish presence inspired the addition of the sweet ham and pork and there is evidence to suggest that the indigenous Taino Indians were adept at making cheese.

There’s a lot to unpack with regards to the Cuban sandwich. There’s so much history, oral and written, conflicting accounts and, in some cases, pure conjecture to consider. A lot of it, like food in general, is tightly woven into the identity of a people, their heritage and cultural pride. The one iteration of this porkalicious treat that bears mentioning above all others is the one that made its way to the shores of Key West, Florida.

The Ultimate Love Story: When Cuban Sandwich Met Cerveza.

A post shared by El Meson de Pepe (@elmesondepepe) on

In the 1870s, in an attempt to flee from the clutches of Spanish rule, many industrious Cubans made a beeline to the nearest land mass where they could re-establish their profitable cigar business and flourish without fear of reprisals. Where did they go? You guessed it.
Before Vicente Martinez Ybor chased his fortune northward to Tampa and became the eponymous founder of a nearby town, he set up shop in Key West first. So, it could be said, the Cuban sandwich was born in Cuba but grew up in the Conch Republic.

“Enough with the history lesson! I’m hungry!” you must be saying.

“Where can I find the best Cuban sandwich in Key West?”
Weighing all the evidence that has been presented and the extensive field tests conducted by this author, I can say without reservation, that the road to Cuban sandwich enlightenment leads only to one place….

El Meson de Pepe

outside dining at el meson de pepe in key west

If you make the USA Today Top 10 Reader’s Choice List, you know you’re doing something right. This sandwich is all the things it’s supposed to be and some of the things it’s not, and that’s a good thing. A very good thing.

Were you to sit in the shade of a lazy palm tree on an empty beach with the sole purpose of concocting the very best Cuban sandwich in the world, there’s a better than average chance that the Cayo Hueso Cuban Mix would have been the result.

First, the bread. The basic building blocks of any sandwich should be able to adequately house the contents within. It should be able to absorb all that goodness without losing its structural integrity. It should be texturally pleasing and, above all, it should be pretty darn delicious. The Cuban Mix ticks all those boxes. Slathered on both sides with butter before it gets the sandwich press treatment, the bread emerges crunchy, with an intoxicating aroma revealing a chewy, pillow-like interior. Gluten-free, this aint.

Then the all-star supporting cast is assembled: A panoply of pork products like sugar-glazed slices from a bone-in ham and luxurious, marinated pork shoulder make an appearance. Slices of young Swiss cheese blanket the meats. To balance all that richness, tangy pickles are applied as are vine ripe tomatoes, both lending a perfect acidity that brightens the whole sandwich. Not considered particularly traditional by some, the Key West version invites shredded lettuce to the party which adds a welcome dimension of freshness and crunch. When it comes to condiments, the obligatory mayo and ballpark yellow mustard is, and should forever be, on every Cuban sandwich no matter where you are.

Regardless of one’s reading of history or bragging rights, the answer to what’s the best Cuban sandwich is simple; it’s the one you like best.