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Caramelized Pineapple Grilled Cheese

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  • Author: Linda
  • Prep Time: 5 minutes
  • Cook Time: 15 minutes
  • Total Time: 20 minutes
  • Yield: 2 sandwiches
  • Category: Lunch, Brunch, Snack
  • Method: Grilling, Stovetop
  • Cuisine: American
  • Diet: Vegetarian

Description

Caramelized Pineapple Grilled Cheese is a sweet and savory sandwich featuring juicy pineapple slices caramelized with brown sugar, paired with melty cheese and crispy golden bread. This tropical twist on classic grilled cheese is bold, indulgent, and irresistibly delicious.


Ingredients

  • 4 fresh pineapple rings or slices
  • 1 tbsp brown sugar
  • 1 tbsp butter (for caramelizing pineapple)
  • 4 slices sourdough or white sandwich bread
  • 4 slices cheese (sharp cheddar, mozzarella, or a mix)
  • 12 tbsp olive oil or additional butter (for grilling)

Instructions

  • In a skillet over medium heat, melt 1 tbsp butter. Add pineapple slices and sprinkle with brown sugar.
  • Cook for 2–3 minutes per side, until caramelized and golden. Remove and set aside.
  • Lay out bread slices and add cheese to each. Place 1–2 caramelized pineapple slices on half of the bread. Top with the other bread slices to form sandwiches.
  • Butter or oil the outsides of the sandwiches.
  • Heat a clean skillet over medium heat and grill sandwiches for 3–4 minutes per side, until bread is golden and cheese is melted.
  • Let rest briefly before slicing and serving.

Notes

  • Try a cheese combo like cheddar and brie for creaminess and contrast.
  • Add bacon or prosciutto for a savory upgrade.
  • For heat, include sriracha mayo or sliced jalapeños.
  • Canned pineapple works in a pinch—just pat dry before caramelizing.
  • Reheat in a skillet, not the microwave, to maintain crispness.