Pressed MagicA search for the best Cuban sandwich in Tampa, the city where it all began

If you'd asked me a year ago, I would have told you that the best Cuban sandwich I ever had was in, of all places, Cambridge, Massachusetts. My sister and I were roommates at the time living in nearby Somerville. We used to hang out at a Franco-Cuban restaurant called Chez Henri, where we'd order mojitos and what amounted to one of the greatest foods we'd ever discovered: Buttery pressed bread, melted cheese, garlicky roasted pork, ham, pickles, and mustard, cut into two triangles, with ribboned plantain chips on the side. It left an indelible impression on us both, and we were pretty much convinced that a better Cuban couldn't possibly exist.

My Massachusetts days are long behind me—I live in New York now, and my sister Shulamit lives with her husband and two kids in Tampa, Florida. There's no shortage of Cuban sandwiches there; in fact, you'll find signs at establishments all around the city flaunting the status of being the "birthplace of the Cubano." On my visits to Tampa over the years, I never took them very seriously, brushing the ads off the way I would any others that claim a superlative. But not too long ago, I made a long overdue visit to Ybor City, Tampa's historic Cuban enclave that at the turn of the last century was the cigar manufacturing capital of the world. There, I was forced to reconsider my skepticism about Tampa's Cuban sandwich. And I decided to eat a few, too.

It turns out that in the late 1880s, Tampa was the recipient of a huge influx of Cuban workers who brought with them their tradition of cigar-making. Ybor City, a municipality named for cigar factory owner Vicente Martinez Ybor, housed the factories, their workers, and the restaurants and food traditions that sprung up around them. While Ybor became a polyglot community of immigrants from around the world working side-by-side in the cigar factories, the flavor of the place remained distinctly Cuban.

Andy Huse, a librarian at the University of South Tampa and a self-proclaimed Cuban sandwich historian, explained to me that while eating establishments did feed workers, female factory employees were discouraged from visiting them, as they served alcohol and were generally considered unfit for a lady. The Cuban sandwich as we know it developed under these circumstances: The easily portable meal was one that men could easily carry with them from the restaurants back to the line, and that cafeteros, coffee carts that kept workers in cafe con leche and other refreshments, would shuttle to the female workers back at the factory.

The Cuban sandwich wasn't always known as a Cuban sandwich: It most likely migrated to Tampa in the guise of the mixto, so-named for its variable combination of meats. (Pork and ham are mandatory; salami appears depending on where you live: It's an essential part of a Tampa Cubano and sacrilege in Miami.) But as it evolved, its components became codified: "Cuban bread, mojo roast pork, ham, salami, swiss cheese, pickles, mustard, mayonnaise on request," Huse recites. He says that by the 1920s and '30s, the sandwich was everywhere in Tampa, the city's contribution to the growing American repertoire of portable, working-class foods, like hamburgers and hot dogs.

Credit: Gabriella Gershenson

Its cigar manufacturing days may be long gone, but Tampa stays true to its history: The city is home to an annual Cubano festival, and in 2012, in a brash challenge to Miami, Tampa named the Cuban its official sandwich. Clearly I had been wrong to skip over the city's Cuban offerings; the thing to do now was to sample them. I piled into the car with my sister's family for a field trip to one of Tampa's most iconic sources for Cubans, The Columbia in Ybor City, an over-the-top Spanish sanctuary and the oldest restaurant in Florida. There, they make their textbook sandwiches with generous quantities of salty meat balanced by mustard and pickle, all on bread from nearby La Segunda Central Bakery, which ended up being the sandwich's finest feature. La Segunda itself is an institution; it's been baking Cuban loaves with the fluffy interior and addictively flakey crust that I couldn't get enough of for more than a century.

Next up was Brocato's, a raucous roadhouse of a sandwich joint that also specializes in another Tampa original, devil crab. Their claim to fame is that they roast their own pork, fragrant with cumin, for their Cubano. (Though that's a selling point today, Huse told me that it was the norm in the early days: "It was an all day thing to make sandwiches," he said. "Eight hours spent making pork, four hours making ham. There was a lot more to it than there is now.") Hoagie-like in its girth and with a refreshing snap from the pickle, Brocato's was the heftiest of the bunch, a Cuban for a sub lover.

Though the relatively thick offerings at The Columbia and Brocato's were satisfying, when it comes to Cubans, I discovered that I fall into the camp of the slim, extreme-pressed, sparsely-filled Tampa Cuban. To me, the most craveable renditions capitalize on the flaky bread, and use the meat, cheese, and fixings as sources of flavor and moisture and little more. The honey Cuban from the West Tampa Sandwich Shop, a tiny cottage of a restaurant, exemplified this style, and hit the Golden Mean with its proportions—crispy, savory, tender, each bite compelling me to take another. I encountered a close second at La Teresita, a family-run Cuban diner with swivel stools and a takeout counter that offered a toasted, slender sandwich with just enough deli meat distraction. But the bread, again, was the star.

Though the formative Cuban of my memory from Chez Henri might always reign supreme (it's hard to compete with nostalgia), eating Cubans in Tampa exposed me to a history I had originally questioned, and an unexpected pleasure I am so glad I now know—Cuban bread, as essential to this place as bagels are to New York or pizza is to Rome. And there's something to be said for getting a specialty at the source, for biting into the original. And let's be honest—no matter where you try it, a Cuban sandwich is going to be pretty darn good.