Hawaiian Grilled Cheese

May 18, 2016 (Last Updated: June 29, 2020)
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A close up of two Hawaiian grilled cheese sandwiches on a board

Today I’m on my way to one of my absolute favorite places: Walt Disney World! I’m particularly excited because for the first time I will be staying at Disney’s Polynesian Village Resort, which has ranked very high on my wish list for years.

two golden brown grilled cheese sandwiches on a white cutting board

I plan on sharing several posts upon my return, discussing the resort as well as all of the amazing food I try during my brief visit to “The Happiest Place on Earth.” Stay tuned!

assembling Hawaiian grilled cheese sandwiches

In the meantime, in honor of Disney’s Polynesian Village Resort, I’ve decided to share a recipe for Hawaiian Grilled Cheese. It’s from an excellent cookbook I recently reviewed, entitled Grilled Cheese Kitchen.

A close up of half-assembled Hawaiian grilled cheese sandwiches

The inspiration for this sandwich derives from Hawaiian pizza—”gooey mozzarella, sweet-tart pineapple, savory ham, and spicy tomato sauce.”

A close up of a halved Hawaiian grilled cheese sandwich on a plate

Although the tomatoes seem a little off-putting at first, they really do make sense in the context of Hawaiian pizza, in terms of the pizza sauce. They add a bit more acidity and sweetness to the sandwich, whereas the tart/sweet pineapple really is the star, along with the salty ham. Baking the sliced pineapple and tomato helps reduce some of the wetness, and yields for a perfectly balanced juicy but not soggy sandwich.

A close up of a cross section of a Hawaiian grilled cheese sandwich

I couldn’t find Hawaiian sandwich bread at my market (only the small slider-sized King’s Hawaiian Rolls), and in the future would plan on baking my own Hawaiian bread. For this endeavor, I opted to use sliced French-style white bread sourced from a local bakery via Whole Foods. It’s a bit crustier than a standard white sandwich bread, but it also boasts a lot more flavor, and a great hearty texture.

A close up of a grilled cheese sandwich with ham, pineapple, and tomato inside

I substituted another great melting cheese, Havarti, for the Fontina specified in the recipe. Honestly, either would be fantastic here, alongside the mild but super gooey fresh mozzarella.

A halved grilled cheese on a plate with ham, pineapple, and tomato filling

This Hawaiian grilled cheese is pretty phenomenal. If you love Hawaiian flavors, this sandwich is definitely for you! It has way more character than your standard grilled cheese, and it’s considerably easy to make.

a closeup of a crispy golden brown Hawaiian grilled cheese sandwich

I can’t wait to share all of my exciting experiences from Disney’s Polynesian Village Resort, and of course the rest of Walt Disney World. Please check back in the coming weeks for my series of posts discussing all the fun and food from my trip!

A close up of a half a Hawaiian grilled cheese sandwich on a white plate
A close up of two Hawaiian grilled cheese sandwiches on a board

Hawaiian Grilled Cheese

This fantastic grilled cheese sandwich is inspired by the flavors of Hawaiian pizza! It features gooey cheese, salty ham, sweet pineapple, and juicy tomatoes.
Prep Time 10 mins
Cook Time 20 mins
Total Time 30 mins
Course Main Course, Sandwich
Cuisine American, Hawaiian
Servings 2 servings
Calories 825 kcal


  • 4 slices fresh pineapple, about 1/4 in [6 mm] thick, cored, or 1/2 of a small can of pineapple rings in juice, drained
  • 6 to 8 slices ripe plum tomato about 1/4 in [6 mm] thick
  • 1 tablespoon salted butter at room temperature
  • 4 slices Hawaiian bread (slightly sweet white bread) or artisan white bread
  • 4 slices (85 g) fontina cheese (I used havarti)
  • 4 oz (115 g) sliced ham
  • 3 oz (85 g) fresh mozzarella cheese, thinly sliced
  • Pinch of red pepper flakes optional


  • 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 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.

Notes & Nutrition

From Grilled Cheese Kitchen
Servings 2.0 * calories 825 * Total Fat 60 g * Saturated Fat 27 g * Monounsaturated Fat 9 g * Polyunsaturated Fat 2 g * Trans Fat 0 g * Cholesterol 184 mg * Sodium 1109 mg * Potassium 262 mg * Total Carbohydrate 73 g * Dietary Fiber 1 g * Sugars 22 g * Protein 66 g
*All nutritional information is based on third-party calculations and should be considered estimates. Actual nutritional content will vary with brands used, measuring methods, portion sizes and more.*

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