Everything you love about the sweet and savory Hawaiian pizza, now in portable grilled cheese form! Turn this classic pizza combination into one heck of a grilled cheese sandwich by using fresh, high-quality ingredients and adding a splash of love.
Preheat the oven to 375°F. Line a baking sheet with parchment paper or aluminum foil.
Arrange the pineapple and tomato slices on the prepared baking sheet and bake for 12 minutes, or until the surfaces appear dry but not yet browned, turning the pieces over halfway through. Remove from the oven and set aside.
Heat a cast-iron or nonstick skillet over medium-low heat.
Spread the butter on one side of each bread slice, dividing it evenly. Place two slices, buttered-side down, on a clean cutting board. Layer two slices of the fontina, half of the ham, three or four slices of roasted tomato, two rings of roasted pineapple, and half of the mozzarella on top of each. Sprinkle with the red pepper flakes (if using). Finish with the remaining slices of bread, buttered-side up.
Using a wide spatula, place both sandwiches in the pan, cover, and cook until the bottoms are nicely browned, about 4 minutes. Turn 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.
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