By Grocery List Plus Editorial Staff | Published on June 14, 2026
Serves 4
1069 cal · 225 min
Cuban Grilled Cheese Sandwich
Recipe GLPR01759c98a32406
A classic Cuban sandwich featuring slow-roasted seasoned pork shoulder, melted Swiss cheese, ham, and pickles pressed on buttered bread and grilled until golden. This version uses tender, flavorful pulled pork as the base, layered with traditional accompaniments for an authentic Caribbean taste.
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Ingredients
3 pounds boneless pork shoulder, trimmed
1 tablespoon kosher salt
1 tablespoon packed light brown sugar
¼ cup water
Swiss cheese slices
sliced ham
dill pickle slices
Cuban bread or sandwich rolls
butter, softened
Directions
Pat the trimmed pork shoulder dry with paper towels. Combine the kosher salt and light brown sugar in a small bowl, then rub the mixture evenly over all sides of the pork.
Place the seasoned pork in a large roasting pan and add the water to the bottom of the pan. Cover tightly with foil and roast in a preheated 325°F oven for about 3 to 3.5 hours, until the pork is very tender and easily shreds with a fork.
Remove the pork from the oven and let it rest for 15 minutes. Shred the pork into bite-sized pieces using two forks, discarding any excess fat. Reserve about 2 cups of the shredded pork for the sandwiches.
Slice the Cuban bread or sandwich rolls lengthwise. Layer the bottom half with shredded pork, then add slices of Swiss cheese, ham, and dill pickle slices. Cover with the top half of the bread.
Butter the outside of each assembled sandwich. Heat a grill pan or skillet over medium-high heat and grill the sandwiches for 3 to 4 minutes on each side, pressing gently with a spatula, until the bread is golden and the cheese is melted.
Transfer the grilled sandwiches to a cutting board, cut diagonally, and serve immediately while still warm.
Comments
The stated 225-minute time is honest only if you're cooking the pork shoulder from scratch; more likely you're using store-bought pulled pork or making this with day-old carnitas, which cuts real prep to under 30 minutes. Swiss cheese, ham, dill pickle, and butter are easy finds at any Charlotte chain, but the pork shoulder itself—whether you're buying it pre-cooked or committing to a slow braise—is the real commitment and cost driver at $12–$18 per pound. The sandwich itself is a same-night, hands-on dish that doesn't reheat well once pressed, so plan to assemble and serve all four at once. For a family willing to prep pork in advance or buy quality deli ham as a shortcut, this is a satisfying weekend lunch; for a weeknight, budget the time and expect to build around the pork, not the other way around.
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