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5 from 2 votes

The Cuban Sandwich

This Cuban sandwich recipe also includes detailed instructions for making pernil, so it leaves you with some extra pork snack on, which is lucky because it’s so good on it’s own! The version we decided to make in our Cubano recipe has a personal, although not original twist: the addition of pepperoni.
Prep Time5 hours
Cook Time1 hour 45 minutes
Total Time6 hours 45 minutes
Course: Sandwich
Cuisine: Cuban
Servings: 4 sandwiches
Author: Bill

Ingredients

For the Roast Pork:

  • a 3 1/2 lb bone-in pork shoulder roast
  • 1 tablespoon salt
  • 1/2 teaspoon black pepper
  • 1 onion (diced)
  • 1 1/2 teaspoons dried oregano
  • 3 cloves minced garlic
  • 1/3 cup orange juice
  • 2 tablespoons lemon juice
  • 2 bay leaves
  • 2 tablespoons olive oil

For the sandwich:

  • 4 sandwich rolls
  • 4 tablespoons yellow mustard
  • 8 slices ham
  • 12 slices pepperoni (optional)
  • 4 thick slices Swiss cheese
  • Sweet pickle slices (we used bread-and-butter pickles)
  • 4 tablespoons softened butter

Instructions

  • Place the pork shoulder in a large heavy duty zip top bag or bowl. Pierce the meat with a sharp knife in several places. In a bowl, combine the salt, pepper, onion, oregano, garlic, orange juice, lemon juice, bay leaves, and olive oil. Pour the mixture over the pork and massage it into the meat, letting the liquid into the holes you'd created with the knife. Let the meat marinate for at least 4 hours or overnight.
  • Preheat the oven to 375 degrees F, and place the roast along with all of the marinade into a roasting pan. Roast for 30 minutes and turn down the heat to 325 degrees F. Continue roasting for another hour or so, basting the roast every 15 minutes. Add about a quarter cup of water if the liquid in the pan dries up.
  • When the pork is done, set aside to rest for 30 minutes and gather the rest of your sandwich ingredients.
  • When you're ready to assemble, slice the rolls in half. Spread mustard on both sides of each roll. Add some of your sliced roast pork and drizzle with some of the drippings from the roasting pan. Add a layer each of ham and pepperoni, if using. Add a slice of cheese, and a layer of pickles. Top with the other slice of bread.
  • Heat a griddle or pan over medium heat. Take each sandwich, and slather butter all over the outside of the bread on both sides. Place on the pan, and cover with aluminum foil and something heavy (like a cast iron skillet) to act as a press. Let cook for about 3-5 minutes, until the bottom is toasty and golden. Flip the sandwiches, cover with the foil and heavy skillet, and cook the other side for another 3-5 minutes, until the sandwich is crispy and the cheese is nice and melted.