This fantastic Hawaiian grilled cheese sandwich is inspired by the flavors of Hawaiian pizza. If you love Hawaiian flavors, this recipe featuring sweet pineapple, salty ham, gooey cheese, and juicy tomato is definitely for you! It has way more character than your standard grilled cheese, and it's considerably easy to make.
Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper or aluminum foil.
Arrange the pineapple and tomato slices on the prepared baking sheet and bake for about 12 minutes, turning the pieces over halfway through, until the surfaces appear dry but not yet browned. Remove from the oven and set aside.
Heat a nonstick skillet or cast iron skillet over medium-low heat.
Spread the soft butter on one side of each bread slice, dividing it evenly. Place 2 slices of bread, buttered-side down, on a clean cutting board. Top each slice of bread with 2 slices of the fontina or Havarti cheese, ½ the ham, 3 or 4 slices of roasted tomato, 2 rings of roasted pineapple, and ½ the mozzarella on top of each. If needed you may cut the pineapple rings a bit to get them to fit nicely. Sprinkle with crushed red pepper flakes, if using. Top with the remaining slices of bread, buttered-side up.
Using a wide spatula, place both sandwiches in the heated pan, cover, and cook until the bottoms are nicely browned, about 4 minutes. Carefully flip over the sandwiches and cook until the second sides are browned, the cheese is melted, and the other ingredients are heated through, about 4 minutes longer.
Cut the sandwiches in half, if desired, and serve immediately.
For the pineapple you may use ¼-inch thick cored slices of fresh pineapple or 4 slices of canned pineapple rings in juice, drained and blotted dry.
I usually opt for Havarti cheese in these sandwiches, but it can be a bit difficult to thinly slice with a knife. You can slice it thicker if needed (and just arrange the thicker slices on your bread to cover the surface) or if push comes to shove you can try grating it too. Either way works! If your deli sells sliced Havarti or fontina cheese, it's much easier than slicing it thinly yourself.
This is a very tall sandwich with a lot of filling, so flipping it over can be challenging without making a mess. I recommend using a spatula to slide it onto a plate, then place another plate (inverted) on top and flip it over between the plates. Then use the spatula to return it to the pan to cook the other side.
Again this sandwich has a thick filling so make sure you cook it on medium-low (or even low) heat covered to help the filling heat through before you flip it over. The thickness of your pan and metal quality will also determine how quickly the bottom browns. Adjust the heat as needed to get a nice dark golden brown with a heated/melted filling.