Recipe: Cuban Grilled Cheese Sandwich

updated Dec 17, 2019
Cuban Grilled Cheese Sandwich
Miami chef Richard Hales puts his spin on the classic Cuban sandwich.

Makes4 large sandwiches

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(Image credit: Tara Donne)

With its combination of tender roasted pork, smoked ham, Swiss cheese, pickles, and mustard, a Cuban sandwich is pretty close to the ideal sandwich. It checks all the right boxes of salty, smoky, meaty, melty, and tangy.

But what if you were to take a classic Cubano and cross it with a grilled cheese? We thought it sounded like a good idea, too, when we spotted it on the menu at chef Richard Hales’ Bird & Bone (the fact that it was served with waffle-cut fries didn’t hurt either).

The biggest difference between your typical Cuban sandwich and Hales’ riff is the choice of bread and the style of grilling; he also throws mayo into the mix and is particular about his ham. But before we dive into the nitty-gritty, let’s back up a bit and take a look at what makes a Cuban sandwich.

What Is a Cuban Sandwich?

A Cuban sandwich is basically the best leftover sandwich of all time. It starts with Cuban roast pork — which you made and ate and loved! — but there was just too much. So you decided to put it on bread along with ham and cheese (why not?), mustard, and thinly sliced pickles. You smoosh the whole thing in a sandwich press and eso.

This is simplifying things a tiny bit, but that is the basic idea: A doubly porky, cheesy, crunchy, ever-so-slightly spicy and acidic sandwich invented (probably) in Florida to feed workers at cigar and sugar factories sometime in the mid-19th century.

Other things to know:

  • The bread is important. The long, rectangular loaves are traditionally made with lard and, before they go into the oven, a palmetto frond is placed on the top. This creates a similar effect to slashing the dough.
  • In Tampa, they add salami to the mix. This addition is, of course, highly controversial if you are not from Tampa.

What Is a Cuban Grilled Cheese Sandwich?

While the sandwich on the menu at Bird & Bone is essentially a Cubano, there are a few key points of difference.

The first is the bread. Hales, who (ahem) hails from Tampa, says that you can’t get good Cuban bread in Miami. We’re guessing there are plenty of Miamians who beg to differ, but his argument is that, in Miami, it isn’t made with lard. So, instead of using Cuban bread, Hales uses medianoche bread. It’s a softer egg bread, similar to challah.

He’s also particular about his ham — he uses Benton’s Country Ham and, if you can get your hands on some, we suggest you do the same. And, while it’s not traditional, he mixes his mustard with a bit of mayo.

Finally, he grills his sandwiches on the stovetop instead of using a panini press. They get buttered up and cooked with a brick on top.

(Image credit: Tara Donne)

Cuban Grilled Cheese Sandwich

Miami chef Richard Hales puts his spin on the classic Cuban sandwich.

Makes 4 large sandwiches

Nutritional Info


For the roast pork:

  • 3 pounds

    boneless pork shoulder, trimmed of excess surface fat

  • 1 tablespoon

    kosher salt

  • 1 tablespoon

    packed light brown sugar

  • 1/4 cup


For the sandwiches:

  • 4

    split medianoche, soft sandwich, or deli rolls

  • 1

    large clove garlic, halved

  • 1/4 cup

    whole-grain mustard

  • 1/4 cup


  • 8

    thin slices Swiss cheese

  • 8 ounces

    sliced pickled onions (about 1 cup), patted dry

  • 6 to 8 ounces

    very thinly sliced pickles

  • 8 ounces

    thinly sliced smoked ham, such as Benton's

  • 8

    thin slices Muenster cheese

  • 4 tablespoons

    unsalted butter, at room temperature


Make the roast pork:

  1. Arrange a rack in the middle of the oven and heat to 375°F. Meanwhile, cut the pork into 2 pieces. Sprinkle all over with the salt and sugar. Place the pieces side by side in an 8- or 9-inch square baking dish. Add the water and cover tightly with the aluminum foil.

  2. Roast for 1 hour. Increase the oven temperature to 450°F. Uncover and roast until the top is golden-brown, about 30 minutes. Flip the pork and roast until the second side is golden-brown and the pork is fork-tender, about 20 minutes more. Set the baking dish aside on a wire rack and let the pork cool slightly while you assemble the sandwiches.

Make the sandwiches:

  1. Open and place the bread rolls cut-side up on a work surface. Gently rub the cut sides of the garlic on the cut sides of the bread, then discard the garlic or save for another use. Spread the mustard on the top halves of the rolls. Spread the mayonnaise on the bottom halves of the rolls.

  2. Place 2 slices of Swiss cheese on the mayonnaise side of each sandwich. Divide the pickled onions over the cheese. Lay a single layer of pickles over the onions. Top with the ham. Using a fork or your fingers, gently shred the roasted pork and place about 3/4 cup evenly on each sandwich (you may have extra pork — save for another use or more sandwiches). Top the roasted pork on each sandwich with 2 slices of Muenster cheese, then close the sandwiches. Press gently on each sandwich to compact slightly. Spread the butter in a thin layer on the outsides of the rolls, spreading on both top and bottom.

For a panini press:

  1. Place the sandwiches in a heated panini press, working in batches if needed, and close. Press until golden-brown on both sides and the cheese is melted, 3 to 5 minutes.

For the stovetop method:

  1. Heat a cast iron skillet or large frying pan over medium heat. Place 2 of the the sandwiches in the pan. Weigh down the sandwiches with an aluminum foil-wrapped brick, or top with another cast iron skillet weighed down with a heavy can. Cook undisturbed until golden-brown on the bottom, 4 to 5 minutes. Flip the sandwiches and cook until the second side is browned, 4 to 5 minutes more.

  1. Cut the sandwiches on the diagonal and serve.

Recipe Notes

Pickled onions: We like the flavor and vibrant color of these pickled onions.

Make ahead: The roast pork can be made up to 3 days ahead, shredded, and refrigerated. The sandwiches themselves are best made and eaten fresh.

Recipes from the Road are recipes gathered from our travels near and far. When you’re there, when you come home, a recipe is always the best souvenir. This month we’re visiting Miami.