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Hawaiian Pizza Grilled Cheese Sandwich

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Hawaiian Pizza Grilled Cheese Sandwich. I remember the first time I melted cheese over a pineapple ring on a weekday evening and my kid grinned like it was a secret. It’s the sort of quick, slightly sticky comfort that lives in real kitchens.

I write this from that same counter, the skillet still warm and a slice cooling on the board. If you like crisp bread with a saucy center, try it on a crusty loaf — I sometimes use a copycat herb bread when I want an extra lift that works well here. Chef Thomas

Why You’ll Love Hawaiian Pizza Grilled Cheese Sandwich

Hawaiian Pizza Grilled Cheese Sandwich is one of those recipes I make when I want something honest and fast. I’ve cooked long enough to know a few small choices change everything, so I keep this simple and repeatable. Chef Thomas

  • Melty, reliable comfort. Cheese and heat are the backbone. They hold the sandwich together and make every bite pull apart nicely.
  • Sweet-salty balance. Pineapple brings brightness and Canadian bacon gives that cured, savory bite without fuss.
  • Kid-friendly, grown-up friendly. It’s easy to involve little hands with assembly, and adults can push it a touch sharper with pepper flakes.
  • Flexible pantry wins. Swap bread or cheese and the core idea still works; the structure stays forgiving.

Ingredients for Hawaiian Pizza Grilled Cheese Sandwich

  • 4 slices sourdough or white bread
  • Butter (for spreading on bread)
  • 1/4 cup pizza sauce (more or less, to taste)
  • 4 slices Canadian bacon
  • 4 pineapple rings (canned or fresh, patted dry)
  • 4 slices Cheddar cheese (or your favorite melting cheese)
  • 🔁 Ingredient Substitutions, Cheddar cheese → Mozzarella (provolone, or Monterey Jack), Canadian bacon → Ham (turkey, or even crispy bacon strips), Sourdough → Brioche (ciabatta, or whole grain sandwich bread), Pizza sauce → Marinara or tomato-basil pasta sauce

These pieces work together the way they should: bread provides the crunch and shell, butter browns the exterior, cheese melts and glues the layers, while sauce and pineapple give moisture and lift. I’ve used these combos for years and they hold up in a skillet, says Chef Thomas.

How to Make Hawaiian Pizza Grilled Cheese Sandwich

Step 1: Prep the bread

Butter one side of each slice of bread. Spread evenly so it browns without burning.

Step 2: Dry the fruit

Pat dry the pineapple rings to prevent sogginess. A paper towel will do.

Step 3: Heat the pan

Preheat a griddle or skillet over medium heat. You want steady, not screaming, heat.

Step 4: 🔥 Cooking Steps

🔥 Cooking Steps

Step 5: Start the sandwich

Place one slice of bread, butter side down, onto the hot griddle. Keep the heat steady.

Step 6: Sauce it

Spread 2 tablespoons of pizza sauce on the unbuttered side. Don’t drown the bread.

Step 7: Add the meat

Layer with 2 slices of Canadian bacon, 2 pineapple rings, and 2 slices of cheese. Stack evenly.

Step 8: Top it

Top with another bread slice, butter side up. Press gently so it holds.

Step 9: First side cook

Cook for 3–4 minutes until golden brown. Watch the edge for color.

Step 10: Flip and finish

Flip carefully and cook for another 3–4 minutes, until cheese is melted and both sides are toasted. Adjust heat if the bread browns too fast.

Step 11: Rest and serve

Remove from pan, let cool slightly, then cut and serve your Hawaiian Pizza Grilled Cheese Sandwich. That cooling step keeps the center from running everywhere.

How I Serve Hawaiian Pizza Grilled Cheese Sandwich

I plate these cut in half on a wooden board most evenings. I like a small dipping bowl of extra warmed pizza sauce on the side for anyone who wants more. Sometimes I set out a tiny bowl of red pepper flakes or chopped fresh basil for people who want to tweak at the table. Chef Thomas

  • A simple green salad or raw carrot sticks for contrast.
  • Sweet potato fries when I want something heartier.
  • A side of pickles for a sharp counterpoint.

I also use the sandwich as a quick party snack. If I’m feeding a crowd, I’ll make several, cut them into thirds, and slide toothpicks through them. For a different handheld idea, I’ll pair it with an easy sheet of rolls inspired by this crescent roll veggie pizza approach when I want to mix textures.

Variations and Adjustments for Hawaiian Pizza Grilled Cheese Sandwich

Cheese choices

Swap Cheddar for mozzarella or provolone if you want a milder, stringier melt. I reach for sharper Cheddar for contrast, but mozzarella keeps the sweetness of the pineapple quieter. Chef Thomas

Protein swaps

Use ham, turkey, or crispy bacon instead of Canadian bacon. Each one changes the chew and salt level, so taste as you go.

Bread and sauce changes

Try brioche for a richer bite or whole-grain for more texture. If your pizza sauce is thick, thin it slightly with a splash of water so the sandwich doesn’t become too wet.

Assembly tweaks

If you’re worried about slipping layers, put the cheese both above and below the pineapple. That creates a cheese “glue” that holds the rings in place while melting. Keep the overall build modest so the bread can close properly.

Storing and Making Hawaiian Pizza Grilled Cheese Sandwich Ahead

Leftovers reheat well if you plan for crispness. I cool sandwiches completely, wrap them in foil, and pop them in the fridge for up to a couple of days. When reheating, return them to a skillet over medium-low heat covered with a lid for a few minutes; that warms the center without turning the bread soggy. Chef Thomas

If you want to make parts ahead, cook the Canadian bacon and pat-dry the pineapple, then store them separately. Assemble and grill just before serving. The only thing I avoid prepping too far ahead is the assembled, ungrilled sandwich — the bread can lose its texture if it sits with sauce too long.

The Small Detail That Makes Hawaiian Pizza Grilled Cheese Sandwich Work

Most people focus on the pineapple or the ham and miss the buttered bread. Browning the outside properly creates a barrier and texture that turns the sandwich from a soggy stack into something you can pick up. I press the sandwich gently while it cooks so the cheese melts evenly and the flavors marry without sliding around. Chef Thomas

Another small thing: patting the pineapple dry is a tiny step that saves you from a steamed, limp interior. It keeps the toast crisp and the cheese melty, which is the real satisfaction. That small care makes the sandwich feel deliberate.

Final Thoughts on Hawaiian Pizza Grilled Cheese Sandwich

Hawaiian Pizza Grilled Cheese Sandwich is a weeknight friend: fast, flexible, and easy to teach to a kid. I make it when I want something that feels special without fuss. Chef Thomas

Conclusion

If you want to see another take on this idea, here’s a different version to compare: Hawaiian Pizza Grilled Cheese Sandwich. For a baker’s spin with photos and tips, look at this write-up: Hawaiian Pizza Grilled Cheese Sandwich – Love Bakes Good Cakes.

Hawaiian Pizza Grilled Cheese Sandwich with ham and pineapple melts
Leann Kirlin

Hawaiian Pizza Grilled Cheese Sandwich

A delightful fusion of Hawaiian pizza flavors and grilled cheese, featuring melty cheese, savory Canadian bacon, and sweet pineapple between crispy, buttered bread.
Prep Time 10 minutes
Cook Time 8 minutes
Total Time 18 minutes
Servings: 2 sandwiches
Course: Lunch, Snack
Cuisine: American, Hawaiian
Calories: 450

Ingredients
  

For the Sandwich
  • 4 slices sourdough or white bread Use a crusty loaf for best results.
  • to taste Butter For spreading on bread
  • 1/4 cup pizza sauce More or less, to taste
  • 4 slices Canadian bacon Can substitute with ham, turkey, or crispy bacon strips
  • 4 rings pineapple Canned or fresh, patted dry to avoid sogginess
  • 4 slices Cheddar cheese Can substitute with mozzarella, provolone, or Monterey Jack

Instructions
 

Preparation
  1. Butter one side of each slice of bread evenly.
  2. Pat dry the pineapple rings with a paper towel.
  3. Preheat a griddle or skillet over medium heat.
Cooking
  1. Place one slice of bread, butter side down, onto the hot griddle.
  2. Spread 2 tablespoons of pizza sauce on the unbuttered side.
  3. Layer with 2 slices of Canadian bacon, 2 pineapple rings, and 2 slices of cheese.
  4. Top with another slice of bread, butter side up. Press gently.
  5. Cook for 3–4 minutes until golden brown, watching for color on the edges.
  6. Flip carefully and cook for another 3–4 minutes, until cheese is melted and both sides are toasted.
  7. Remove from pan, let cool slightly, then cut and serve.

Notes

For serving, toast with a small side of extra warmed pizza sauce and red pepper flakes or chopped fresh basil. Consider side options like a green salad or sweet potato fries for contrast.

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About CHEF THOMAS

Chef Thomas, recipe developer and home cooking expert

My name is Chef Thomas, creator and owner of Tomatillo Recipes. As a classically trained chef with over 40 years of experience, I develop and test time-tested tomatillo recipes and share practical chef tips to help you create flavorful, reliable meals in your home kitchen.

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