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.

Two halves of a Hawaiian grilled cheese stacked on top of each other on a plate.

(This recipe was originally published in May 2016, but was updated with new photos and content in 2021).

When it comes to Hawaiian pizza you either love it or hate it. I am 100% solidly on Team Hawaiian Pizza. I absolutely LOVE the combination of juicy sweet pineapple and salty ham bound together with melted cheese on a crispy crust. The opportunity to use these flavors in a phenomenal grilled cheese sandwich is one I simply can't resist!

Tomatoes add a bit more acidity and sweetness to the grilled cheese sandwich, whereas the tart/sweet pineapple really is the star along with the ham. Baking the sliced pineapple and tomato helps reduce some of the wetness. This yields a perfectly balanced juicy but not soggy sandwich.

Ingredient notes

Tomatoes, sliced pineapple, sliced bread, ham, cheeses, and a bottle of crushed chili flakes.

Bread: Ideally use sliced Hawaiian bread (such as King's Hawaiian) for these Hawaiian grilled cheese sandwiches. If you can't find this or don't want to bake Hawaiian bread from scratch you can easily use sliced artisan white bread. Both options are equally delicious!
Pineapple: For the pineapple component you may use ¼-inch thick cored slices of fresh pineapple or 4 slices of canned pineapple rings in juice, drained and blotted dry.
Ham: Use your favorite ham for these pineapple and ham grilled cheese sandwiches. You could use thinly sliced homemade leftover baked ham or opt for something like a honey ham or Black Forest ham from the deli for a pretty classic flavor.
Tomato: Plum or Roma tomatoes are ideal for this Hawaiian grilled cheese recipe because they are a bit less juicy with less seeds. They are easier to dry out in the oven to keep the sandwich from becoming soggy.
Cheese: Use a mild to medium-sharp melting cheese like fontina or Havarti alongside mild but super gooey and stretchy fresh mozzarella for this sandwich.

A halved grilled cheese sandwich on a plate showing off the ham and pineapple filling.

How to make it

Preheat the oven to 375°F and line a baking sheet with parchment paper or aluminum foil. Arrange the pineapple and tomato slices on the baking sheet and bake, turning the pieces over partway through, until the surfaces appear dry but not yet browned. Remove from the oven and set aside.

Before and after photos of roasting tomato and pineapple slices on a sheet pan.

Heat a nonstick or cast iron skillet over medium-low heat.

Spread 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 sliced fontina or Havarti cheese, sliced ham, roasted tomato, roasted pineapple, and sliced fresh mozzarella. Sprinkle with crushed red pepper flakes, if using.

Closeup of an assembled but uncooked Hawaiian grilled cheese with layers of ingredients.

Top 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. Carefully flip over the sandwiches and cook until the second sides are browned, the cheese is melted, and the other ingredients are heated through.

Cut the Hawaiian grilled cheese sandwiches in half, if desired, and serve immediately.

Please scroll to the bottom of the post for the full recipe (in a printable recipe card) including ingredient amounts and detailed instructions.

Closeup of a grilled cheese sandwich with ham and pineapple in the filling.

Expert tips

I usually opt for Havarti cheese in these pineapple and ham grilled cheese 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 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.

A halved Hawaiian grilled cheese sandwich on a plate showing off the ham and pineapple filling.

Other recipes you may like

Spanglish Sandwich (BLT with Egg and Cheese)
Strammer Max (German Open-Faced Ham Sandwich)
Don Gondola Italian Grilled Cheese
Mushroom Gruyère Grilled Cheese
Grilled Cheese with Tomato, Pesto, and Olive Tapenade
Hawaiian Hot Dog (with Pineapple Relish)
Authentic Hawaiian Macaroni Salad
Hawaiian Loco Moco (Hamburger Steak with Gravy)
HippopotoMai-Tai (from Trader Sam's at Disney)
Hawaiian Butter Mochi

Tried this recipe? Please leave a star ⭐️⭐️⭐️⭐️⭐️ rating in the recipe card below and/or a review in the comments section further down the page. You can also follow me on social media on Facebook, Instagram, and Pinterest!