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+ servings

The Ultimate Hawaiian Grilled Cheese

Author - Serena Wolf
Prep Time: 15 minutes
Cook Time: 15 minutes
Yields: 2 sandwiches


  • ½ pineapple peeled, cored and cut into ½ inch planks
  • Kosher salt
  • 4 slices multigrain bread
  • 2 tablespoons softened butter
  • cups shredded part-skim mozzarella cheese
  • 1/3 pound prosciutto di Parma
  • ¼ cup fresh basil chopped
  • Marinara or arrabiata sauce for dipping


  • Start with the pineapple. Peel and core the pineapple (you can usually find peeled, cored pineapple at the market to make things easier), and cut ½ of the pineapple into planks about ½ inch thick. Season each plank with a little kosher salt.
  • Heat a grill or grill pan over medium-high heat. When hot, add the pineapple and cook for about 3 minutes on each side until sexy grill marks appear and the fruit is lightly caramelized. Briefly set aside.
  • Now it’s time to assemble the grilled cheese. To assemble each sandwich: Butter one side of each piece of bread with ½ tablespoon softened butter and place the bread butter-side down on a cutting board. Top one piece of bread with about ¼ cup cheese and add a layer of prosciutto. Sprinkle another 2 tablespoons of cheese on the prosciutto and add half of the grilled pineapple and half of the basil. Sprinkle with another 2 tablespoons of cheese and add another layer of prosciutto. Add the remaining ¼ cup cheese and top with the second piece of bread (buttered side facing out).
  • Heat a large non-stick pan or skillet over medium heat. When hot, add the sandwiches and cover with a lid. Cook for about 4 minutes until the underside is golden brown. Flip the sandwiches and chook for 3-4 minutes more.
  • Remove your epic grilled cheese from the pan and serve immediately with tomato sauce for dipping.