Cuban Grilled Cheese
Recipe by Steven Weitzman, founder & head chef of Grilly CheesePublished 2026-10-26Updated 2026-10-26
Cuban grilled cheese with quick-seared pork, ham, Swiss, mustard, and dill pickles. A home skillet adaptation with clear pork temperature and resting instructions.
Cuban grilled cheese is a crisp skillet sandwich layered with pork, ham, Swiss, mustard, and dill pickles, bringing savory, tangy flavor to a quick lunch. This home adaptation uses thin pork tenderloin slices and standard sandwich bread so you can cook it in one skillet. The pork cooks before assembly, then rests while the other ingredients wait. Dry pickles and thin layers help the sandwich hold together, and gentle pressure brings the filling into contact with the melting cheese. Makes: 2 sandwiches. Time: 10 minutes prep, about 16 minutes cooking, and 4 minutes resting, for about 30 minutes total. Timing includes a 3-minute pork rest and a 1-minute sandwich rest, and assumes both sandwiches fit in the skillet.
How to make Cuban Grilled Cheese
Makes 2 sandwiches. Listed times are estimates; visual and temperature cues control doneness.
10 minCook
16 minRest
4 minTotal
30 minYield
2 sandwiches
Equipment
- 12-inch skillet or griddle
- Wide spatula and tongs
- Instant-read food thermometer
- Clean plate for cooked pork
- Cutting board and knife
- Paper towels
Ingredients
- •4 ounces pork tenderloin, trimmed and sliced crosswise 1/4 inch thick
- •1/4 teaspoon garlic powder
- •1/8 teaspoon fine salt
- •1/8 teaspoon ground black pepper
- •1 teaspoon neutral cooking oil
- •2 ounces thinly sliced fully cooked deli ham
- •4 thin lengthwise dill pickle sandwich slices, patted dry
- •4 slices sturdy white sandwich bread, about 1/2 inch thick
- •2 tablespoons unsalted butter, softened
- •2 teaspoons yellow mustard
- •4 ounces Swiss cheese, thinly sliced
Instructions
- 1
Sear and rest the pork
Season the pork slices with the garlic powder, salt, and pepper. Heat the oil in a 12-inch skillet over medium-high heat. Add the pork in one layer and cook for about 2–3 minutes per side, until lightly browned and each piece reaches 145°F in the center. Insert the thermometer sideways into the thin slices. Transfer to a clean plate and rest for at least 3 minutes before cutting into thin strips. Use clean utensils and a clean board for the cooked meat. Lower the skillet to medium-low, warm the ham for about 1 minute, then transfer it to the plate. Wipe the pan clean using a folded paper towel held in tongs.
- 2
Layer the meats, pickles, and Swiss
Pat the pickle slices dry. Spread the butter evenly over one side of all four bread slices. Place two slices buttered-side down on a clean board and divide half the Swiss between them. Divide the pork and ham over the cheese, add two pickle slices to each sandwich, and top with the remaining Swiss. Spread 1 teaspoon mustard on the unbuttered side of each remaining bread slice, then close the sandwiches with the buttered sides out.
- 3
Grill with gentle pressure
Keep the skillet over medium-low heat, letting it cool briefly if it is still very hot from searing. Add both sandwiches if they fit without crowding. Cook for 4–5 minutes per side until golden, the Swiss has melted, and the filling is hot throughout. Press gently with a wide spatula for a few seconds on each side to bring the layers together. Lower the heat if the bread browns too quickly. Transfer to a board, rest for 1 minute, then cut and serve. A second batch adds 8–10 minutes if both sandwiches do not fit.
Variation
- Bread: Use standard-size sourdough slices of a similar thickness. - Mustard: Dijon can replace yellow mustard, giving a sharper flavor. - Pickles: Use enough thin dill pickle rounds to cover each sandwich in one layer, drying them well. - Cheese: Mild provolone melts well at the same weight, though it changes the Swiss flavor.
Questions and answers
What is in a Cuban grilled cheese?
This version contains pork, ham, Swiss, yellow mustard, and dill pickles inside buttered sliced bread. It is a home skillet adaptation with quick-cooked pork tenderloin.
What cheese is best for Cuban grilled cheese?
Swiss pairs well with the salty ham, pork, and tangy pickles. Thin slices melt more evenly around the filling.
Do I need a sandwich press?
No. A skillet and wide spatula work. Press gently for a few seconds on each side while the bread grills.
Can I put raw pork directly inside the sandwich?
Cook the pork separately to 145°F and rest it for at least 3 minutes before assembly. The final grilling stage crisps the bread and melts the cheese.
How do I keep pickle sandwiches from getting soggy?
Use thin slices and blot away brine before building. Keep the filling in even layers and grill just before serving.
Why is the bread browned before the Swiss melts?
The skillet is too hot or the filling is piled too high. Lower the heat after cooking the pork and use thin, even layers.
Storage and reheating
Grilled cheese is best eaten right away. Refrigerate leftovers promptly in a covered, shallow container at 40°F (4°C) or below, within 2 hours of cooking—or within 1 hour when the temperature is above 90°F (32°C). Use within 3–4 days. Reheat to 165°F (74°C), checking the center with a food thermometer. A skillet over low heat, briefly covered and then uncovered, can warm the center and help restore the crust. If using previously cooked chicken or other leftovers, count storage time from when that ingredient was first cooked. See USDA leftovers guidance and FoodSafety.gov minimum temperatures.
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