Get ready to elevate your grilled cheese game with this Cheese Crusted Hawaiian Grilled Cheese! This isn’t your ordinary sandwich—it combines the nostalgic comfort of a classic grilled cheese with tropical Hawaiian flavors and a mind-blowing crispy cheese crust on the outside.
Inspired by both diner-style patty melts and Hawaiian pizza, this sandwich features sweet pineapple, savory ham, and gooey melted cheese, all encased in bread that’s been crusted with even more cheese. It’s the perfect balance of sweet, salty, and utterly indulgent.
Why You’ll Love This
- The crispy cheese crust adds an incredible texture contrast to the melty interior
- Sweet pineapple and savory ham create a perfect flavor balance
- Can be prepped in advance and cooked when you’re ready
- Impressive enough for guests but easy enough for a weeknight dinner
- Customizable with different cheese varieties to suit your taste

Ingredients
- 2 slices thick sourdough bread
- 2-3 slices extra thin deli ham
- 1 slice canned pineapple, or ¼ cup pineapple chunks
- 1 cup shredded mozzarella cheese, divided
- ½ teaspoon dried oregano
- 2 tablespoons salted butter
Instructions
- Lay one slice of bread flat and layer with ham slices and pineapple. Sprinkle about ½ cup of shredded mozzarella over the pineapple, then add a pinch of dried oregano for extra flavor.
- Place the second slice of bread on top to complete the sandwich. Generously sprinkle the remaining mozzarella cheese over the top slice of bread – this will create the crispy cheese crust.
- Melt butter in a nonstick skillet or cast iron pan over medium-high heat. Make sure the butter coats the entire bottom of the pan evenly.
- Carefully place the sandwich in the hot skillet with the cheese-topped side facing up. Cook for 3-5 minutes until the bottom slice turns golden brown and crispy.
- Using a spatula, carefully flip the sandwich so the cheese side is now down against the hot pan. Cook for another 3-5 minutes until the cheese forms a golden, crispy crust and the inside cheese is completely melted.
- Remove from heat and let cool for just 30 seconds before cutting. Slice diagonally and serve right away while the cheese is still gooey inside and crispy outside.
Tips & Variations
- For extra flavor, spread a thin layer of Dijon mustard on the inside of the bread
- Try using canned pineapple tidbits if fresh isn’t available (just drain and pat dry first)
- Substitute Canadian bacon or bacon for the ham if preferred
- Add a few thin slices of jalapeño for a spicy kick
- Use a panini press for even cooking (just add the cheese crust right before pressing)
- Make it vegetarian by omitting the ham and adding extra vegetables like bell peppers
Serving Suggestions
Serve these indulgent sandwiches with a light side like a simple green salad dressed with vinaigrette to balance the richness. For a more substantial meal, pair with a cup of tomato soup for the ultimate comfort food combination.
These sandwiches are best enjoyed fresh off the skillet when the cheese crust is at its crispiest and the interior is perfectly melty.
Notes
- The key to the perfect cheese crust is using a non-stick pan and medium heat – too hot and the cheese will burn before melting properly
- If making for a crowd, keep finished sandwiches warm in a 200°F oven while preparing the rest
- For the best texture, dice the pineapple into small pieces (about 1/4 inch) so they distribute evenly
FAQs
Can I make these ahead of time?
You can assemble the sandwiches up to a day ahead, but add the cheese crust just before cooking for the best results.
What’s the best bread to use?
Sourdough works beautifully for its flavor and sturdiness, but any thick-cut bread will work. Avoid very soft bread that might get soggy.
Can I use pre-shredded cheese?
Yes, but freshly shredded cheese melts better. Pre-shredded cheese contains anti-caking agents that can affect the melt and crust formation.
How do I know when my sandwich is done?
The outside should be golden brown and crispy, and when you lift a corner, the cheese inside should be completely melted.
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