Hawaiian Grilled Cheese
Recipe by Steven Weitzman, founder & head chef of Grilly CheesePublished 2026-10-27Updated 2026-10-27
Hawaiian grilled cheese with browned pineapple, ham, cheddar, and Monterey Jack. Make two crisp skillet sandwiches with a simple pineapple-drying step.
Hawaiian grilled cheese is a sweet-savory sandwich of ham, pineapple, and melted cheese on golden toasted bread, made for a quick skillet lunch with a warm, fruity filling. This version browns drained pineapple before assembly to remove surface moisture and develop flavor. Cheddar adds a familiar sharp note, while Monterey Jack melts around the ham and fruit. The name describes the popular ham-and-pineapple combination used here; this is an American-style grilled cheese recipe. Makes: 2 sandwiches. Prep: 8 minutes. Cook: about 20 minutes. Rest: 1 minute. Total: 29 minutes. Use a 12-inch skillet that fits both sandwiches; a smaller pan needs another grilling batch and more time.
How to make Hawaiian Grilled Cheese
Makes 2 sandwiches. Listed times are estimates; visual and temperature cues control doneness.
8 minCook
20 minRest
1 minTotal
29 minYield
2 sandwiches
Equipment
- Can opener
- Strainer
- Paper towels or clean kitchen towel
- 12-inch nonstick skillet
- Flexible spatula
- Tongs
- Clean plate
- Cheese grater
- Measuring spoon
- Butter knife
- Cutting board and knife
Ingredients
- •4 canned pineapple rings packed in juice, drained, about 5 ounces (140 g) drained weight: Choose thin, standard canned rings. Their weight varies by brand; four rings are the main measure.
- •4 ounces (115 g) thinly sliced fully cooked ham: Separate the slices before warming.
- •2 ounces (55 g) medium cheddar, freshly grated, about 1/2 cup
- •2 ounces (55 g) Monterey Jack, freshly grated, about 1/2 cup
- •4 slices sturdy white sandwich bread, about 1/2 inch thick
- •2 tablespoons softened unsalted butter
Instructions
- 1
Brown the pineapple and warm the ham
Pat the drained pineapple rings thoroughly dry. Heat a 12-inch nonstick skillet over medium heat. Add the rings in one layer and cook for 2–3 minutes per side until golden-brown patches appear and the surfaces look drier. Transfer to a clean plate and cut each ring in half. Add the ham to the skillet, turning for 1–2 minutes until steaming hot throughout; transfer to the plate. Reduce the heat and wipe the skillet with a paper towel held in tongs to remove sticky pineapple residue.
- 2
Layer the filling
Mix the grated cheddar and Monterey Jack. Spread the butter evenly over one side of all four bread slices. Place two slices butter-side down on a board. Top each with one-quarter of the cheese mixture, half the ham, four pineapple half-rings arranged flat with minimal overlap, and another quarter of the cheese. Close with the remaining bread, butter-side out.
- 3
Grill until golden
Set the skillet over medium-low heat. Add both sandwiches and cook for 4–5 minutes per side, flipping carefully, until the bread is golden and the cheese has melted throughout. Lower the heat if the bread darkens before the cheese melts. Transfer to a board, rest for 1 minute, then cut and serve. Allow about 20 minutes for the full cooking sequence.
Tips
- →Press the pineapple gently between towels before it reaches the pan. Avoid squeezing so hard that the rings break.
- →Let the rings sit for a couple of minutes before turning so the surfaces can brown.
- →Lower the heat if pineapple sugars begin turning black. Golden patches give flavor; scorched residue tastes bitter.
- →Wipe out sticky residue before grilling the sandwiches so it does not burn onto the bread.
- →Arrange the pineapple half-rings in a flat layer, trimming pieces to fit if necessary. A tall mound makes flipping harder.
- →Keep the ham and fruit inside the bread edges and use a broad spatula for turning.
- →Rest briefly before cutting so the melted cheese holds the filling together.
Variation
Fresh pineapple: Use four thin, cored rings about 1/4 inch thick. Pat dry and brown until the surfaces look drier; fresh fruit may need extra cooking time. Pineapple pieces: Use about 5 ounces (140 g) drained canned pineapple pieces in place of the rings. Cut large pieces smaller, pat dry, brown in the skillet, and arrange in one even layer. Cheese: Replace the cheddar and Monterey Jack with 4 ounces of either cheese alone. Mild provolone also works. Bread: Sourdough or sliced whole-wheat bread of similar thickness can replace the white bread. Oversized slices may require grilling one sandwich at a time.
Questions and answers
What goes in Hawaiian grilled cheese?
This version combines ham, pineapple, cheddar, and Monterey Jack between buttered bread slices. The pineapple is dried and browned first, then the assembled sandwich is grilled until golden.
Can you use canned pineapple in grilled cheese?
Yes. Drain it thoroughly and pat it dry before browning it in the skillet. Pineapple packed in juice works well for this recipe.
How do you stop pineapple grilled cheese from getting soggy?
Remove surface juice from the pineapple and cook it briefly before assembly. Keep the filling flat and serve the sandwich soon after grilling.
What cheese goes well with ham and pineapple?
Medium cheddar adds flavor, and Monterey Jack gives a smooth melt. You can use either alone or combine them as this recipe does.
Do I need to cook the ham before making the sandwich?
Use fully cooked ham and warm it in the skillet before assembling. This helps the filling become hot without over-browning the bread; raw pork is not a direct substitute.
Can I make Hawaiian grilled cheese ahead of time?
You can brown the pineapple and refrigerate it with the cooked ham in a covered container, then reheat the filling thoroughly before assembling. Grill the bread just before serving for the best crust.
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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