
Cheesy crust Hawaiian grilled cheese flips the classic into a sunshine-filled sandwich. The outside gets crunchy and browned, while ham and pineapple inside hit you with juicy, sweet, and salty bites. If you want comfort food that feels like a little vacation, you’ll be grinning at every bite.
I started making this one gloomy Saturday when I needed something cozy. I had some leftover ham and found pineapple in the cupboard. The cheese outside won me over right away. Now it’s one of our go-to lunch ideas at home.
Irresistible Ingredients
- Salted butter: Makes that golden crunch on the outside. Pick real butter for some epic flavor.
- Dried oregano: Sprinkling a pinch gives every bite a little Italian kick.
- Shredded mozzarella cheese: The best for melting easily and creating a crispy shell. Doing it fresh is always better if you can.
- Canned pineapple or chunks: Adds sweet and tart to each mouthful. Go for ones packed in juice, and let them drain well so your sandwich stays firm.
- Extra thin ham: The saltiness and deep flavor come from this. Grab some quality deli ham with no weird extras.
- Sourdough bread: Holds together against gooey cheese and juicy pineapple. Go for that tang and a crunchy edge.
Simple Steps to Make It
- Serve:
- Slice the hot sandwich in half for that dreamy melty cheese moment Eat it right away for best crunch and flavor
- Flip for Cheese Crust:
- Flip so the cheesy side faces the skillet now Wait three to five minutes while the cheese gets a golden crisp Press down a bit with a spatula for even crunch
- Grill the Sandwich:
- Set your sandwich cheese side up on the pan Grill three to five minutes until the bottom crisps and cheese inside goes melty
- Butter and Heat:
- Throw a blob of butter into a pan over medium-high heat Let it get foamy but don’t let it turn brown
- Build the Sandwich:
- Put the second bread slice over the top with a little press Add a handful more mozzarella to that top slice so you’ll get a cheese crust
- Season:
- Shake dried oregano on the cheesy layer to give it that nice herby punch
- Add Cheese:
- Sprinkle a big helping of mozzarella over the pineapple and ham Press gently so nothing slides around
- Prepare the Filling:
- Lay out a sourdough slice and pile on ham and pineapple in a nice even layer so every bite has both This also helps keep things from getting soggy

The cheesy outside is my favorite part. It’s almost like the crunchy bits on a pizza, but you get them so fast on the stove. The sweet pineapple always takes me back to lazy afternoon lunches by the beach with my folks.
Smart Storage Ideas
Honestly, grilled cheese is best the second it’s off the pan if you love the crunch. But if you need to save one, let it cool, wrap it tight, pop it in the fridge for a day tops. To get back the crunch, reheat in a dry pan on medium heat.
Swap Outs
No sourdough? Thick white or multigrain bread will do just fine. Out of mozzarella? Monterey Jack or provolone melt great too. Want it vegetarian? Skip ham—use more pineapple and sliced grilled peppers.
How to Serve It Up
Toss it next to a bowl of tomato soup or a crunchy green salad for a chill meal. For more island flavor, throw some fresh pineapple slices on the plate too.

Backstory and Fun Facts
Grilled cheese has been an American comfort standby forever. Adding ham and pineapple? That’s borrowed from Hawaiian pizza. The outside cheese crust is a fun cooking trick that’s popped up lately and totally changes the vibe.
Recipe FAQs
- → Which bread is sturdy enough for this sandwich?
Sourdough works great! It holds the fillings well and adds a tasty bite.
- → Will fresh pineapple work instead of canned?
Of course! Fresh pineapple gives it extra zing. Just cut thin slices for easy grilling.
- → What other cheeses melt well for this sandwich?
Cheddar, provolone, or gouda are all great options if you're in the mood for something different.
- → How can I make the cheese crust crunchy?
Press shredded cheese onto the outer sides of the bread and grill on medium. It'll turn golden and slightly crisp.
- → Is a panini press okay to use for this?
Definitely! A panini press crisps up the outer crust perfectly and cooks the inside evenly.