Hawaiian Pizza Grilled Cheese

This Hawaiian Pizza Grilled Cheese Sandwich transforms two beloved comfort foods into one irresistible meal. The sweet pineapple and savory Canadian bacon create that classic Hawaiian pizza flavor profile, while the grilled bread delivers the satisfying crunch and buttery goodness you crave from a perfect grilled cheese.

I created this recipe when my kids were going through a picky eating phase. They loved both pizza and grilled cheese separately, so combining them was my sneaky way to introduce new flavor combinations. Now it's our go-to Friday night dinner when we want something fun but don't feel like ordering takeout.

Ingredients

• Sourdough or white bread provides the perfect canvas and adds a satisfying crunch when grilled
• Butter creates that golden exterior and rich flavor that makes grilled cheese irresistible
• Pizza sauce adds tanginess and authentic pizza flavor without making the bread soggy
• Canadian bacon offers a leaner alternative to traditional ham while providing that classic Hawaiian pizza taste
• Pineapple rings bring natural sweetness and juiciness that complements the savory elements
• Cheddar cheese melts beautifully and its sharp flavor stands up well to the other bold ingredients

Step-by-Step Instructions

Preheat the Skillet

Heat your griddle or skillet over medium heat. This temperature is crucial as it allows the bread to toast slowly while giving the cheese enough time to melt completely. Too hot and your bread will burn before the cheese melts. Too cool and your sandwich will be soggy.

Butter the Bread

Spread a thin but complete layer of butter on one side of each bread slice. Make sure to cover edge to edge for even browning. Using softened butter makes this much easier than trying to spread cold butter which can tear the bread.

Assemble the Sandwich

Place one slice of bread butter side down on your heated surface. This is when you need to work relatively quickly. Spread about 2 tablespoons of pizza sauce in an even layer leaving a small border around the edges to prevent oozing. Layer your Canadian bacon slices so they cover the entire bread surface. Add pineapple rings next distributing them evenly. Top with Cheddar cheese slices and finish with the second slice of bread butter side facing up.

Grill the Sandwich

Let the sandwich cook undisturbed for 3 to 4 minutes. Resisting the urge to peek or press down initially helps the bottom develop that perfect golden crust. Once the bottom is beautifully browned carefully flip the entire sandwich using a wide spatula. Cook the second side for another 3 to 4 minutes until it matches the first side in color and the cheese is completely melted.

Repeat and Serve

Remove your finished masterpiece and begin the second sandwich while the first one rests briefly. This short rest allows the molten cheese to set slightly so it doesn't completely run out when you cut it. Slice diagonally for maximum cheese pull effect and serve while still warm.

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The Canadian bacon in this recipe is my secret weapon. Unlike regular bacon which can sometimes overpower with its smokiness Canadian bacon has a more ham like quality that complements the pineapple perfectly. I discovered this by accident when I ran out of regular ham one day and my family actually preferred the Canadian bacon version.

Managing Moisture

The biggest challenge with this sandwich is managing moisture, especially from the pineapple. Always pat your pineapple rings thoroughly with paper towels before adding them to your sandwich. If using canned pineapple drain it well and let it sit on paper towels for about 10 minutes. Too much moisture will make your bread soggy and prevent that perfect crispy exterior from forming.

Make Ahead Tips

While grilled cheese is best eaten fresh you can prep components ahead of time to make assembly lightning fast. Cook Canadian bacon in advance and store in the refrigerator. Measure out your pizza sauce into small containers. Have your cheese sliced and ready to go. With these preparations you can have this sandwich ready in under 10 minutes whenever a craving strikes.

Flavor Variations

This sandwich concept is endlessly adaptable based on your favorite pizza toppings. Try a Meat Lovers version with pepperoni Canadian bacon and cooked sausage. For vegetarians substitute the Canadian bacon with sautéed mushrooms and bell peppers. Love spice? Add jalapeño slices or red pepper flakes to the pizza sauce. The foundation of bread cheese and sauce provides the perfect base for experimentation.

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Commonly Asked Questions

→ Can I use different types of cheese for this sandwich?

Absolutely! While the recipe calls for Cheddar, you can substitute mozzarella or provolone for a more authentic pizza flavor. Other melty cheeses like Monterey Jack or Havarti would also work beautifully.

→ How do I prevent the sandwich from becoming soggy?

The key is to pat the pineapple rings thoroughly dry before adding them to your sandwich. You can also limit the amount of pizza sauce or spread it only in the center of the bread, leaving a border around the edges.

→ What's the best bread to use?

Sourdough provides excellent structure and a complementary tangy flavor, but any sturdy bread works well. White bread offers a classic approach, while heartier options like whole grain add nutrition and texture.

→ Can I make this in a panini press instead of a skillet?

Yes! A panini press works wonderfully and creates even heating on both sides simultaneously. Butter the outside of the bread as usual, assemble your sandwich, and press until golden and crispy, typically 3-5 minutes.

→ What sides pair well with this sandwich?

Simple sides work best to complement the bold flavors. Try potato chips, a side salad with vinaigrette, pickles, or a small cup of tomato soup for dipping. For a Hawaiian-themed meal, serve with fresh tropical fruit.

→ Can I use fresh pineapple instead of rings?

Yes, fresh pineapple chunks or slices work well. Just be sure to cut them thinly and pat them extremely dry to remove excess moisture. Fresh pineapple tends to be juicier than canned, so this step is especially important.