Hawaiian Grilled Cheese
Hawaiian Grilled Cheese: These grilled cheese dippers have comfort written all over them!
Sundays were made for things like chocolate cake, cheesy pizza, all the coffee lattes, and major relaxation/vegging with books, TV shows, and all the pinteresting.
And grilled cheese, of course. Lots and lots of grilled cheese. This weekend we’re having a lot of cheese with our bread. Actually, allllll of the cheese please, because grilled cheese is not the time for holding back the calories. There’s a time and a place for healthy eating, like with this recipe, and this one, and this one too.
But when it comes to grilled cheese, umm, more cheese please.
I love a good, classic grilled cheese. Sometimes you can’t beat a toasted cheesy sandwich. And when dipped (which is so easy when the grilled cheese is sliced in strips) in soup? It’s the complete rainy day meal.
However, I love taking the classic and turning it into something out of the box, like this Lasagna Grilled Cheese. Today, though, I was in the mood for the tropics. A little aloha oasis, if you will, with this Hawaiian grilled cheese. I’ve never had the opportunity to visit Hawaii, and I have a feeling this probably isn’t classic Hawaiian fare, but I felt a little tropical eating this.
The components of this sandwich are: cheese (cheddar and pepperjack, to be exact), smoked ham, canadian bacon (or turkey bacon or pork bacon), and pineapple. I used regular sandwich bread, as it was all I had on hand, but this would be perfect with sourdough bread or Texas toast.
To make this grilled cheese, all you do is butter one side of each bread, layer the sandwich with cheddar cheese, ham, canadian bacon, pineapple, and pepperjack cheese. Cook on med/low heat until golden brown. Flip and cook until the other side is golden brown and the cheese is melty.

Hawaiian Grilled Cheese
Ingredients
- 4 slices of bread
- 2 slices cheddar cheese
- 2 slices pepperjack cheese
- 4 pineapple rings
- 4 slices of smoked ham
- 4 slices of canadian bacon, cooked if it already isn't (or pork or turkey bacon, cooked)
- 2 Tbsp butter
Instructions
- Spread one side of each piece of bread with butter, about 1/2 Tbsp per slice.
- To build the sandwiches, lay two slices of bread out, unbuttered sides down.
- Lay a slice of cheddar on each, 2 slices of smoked ham on each, 2 slices of canadian bacon on each, two pineapple rings on each, and each with a slice of pepperjack. Top with remaining two slices of bread, buttered side up.
- Over medium/low heat, cook the sandwiches until golden brown, about 3-4 minutes. Flip, and cook the other side until golden brown and the cheese is melting, about 3-4 minutes.
- Cut into strips, if you want them as dippers, or keep it whole.
- Enjoy!
The nutrition facts provided are calculated using a third-party tool and are estimates only. Actual nutritional content may vary based on the ingredients and brands you use, as well as portion sizes. For accurate results, please consult a registered dietitian or nutritionist.

Meet Michelle
I’m a self-taught baker who truly believes it’s impossible to be upset when eating dessert. It’s my life’s goal to bake everyone happy!
If I’m not baking, I’m probably reading a good book with a cup a coffee in hand.
Welcome! I’m glad you’re here!
I love stuffing grilled cheese with all KINDS of stuff! This combination looks incredible!
Thanks, Ashley!
I am in heaven! Ingenious! Pinned!
Thanks, Sara!
no, i’ve never seen anything like this in Hawaii, but who cares?!!! These look so yummy and so much fun!!! Fabulous!
Thanks so much, Mimi! 🙂
This grilled cheese looks soooo good…. that cheese!! Gimme!
Thanks so much! 🙂