Caribbean Grilled Double Cheese Sandwich

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caribbean grilled double cheese sandwich

This Caribbean grilled double cheese sandwich is something that you’d never expect to taste when you bite into it!

Pineapple Cheese Sandwich

Pineapple is one of the sweetest fruit ever established. And, it’s perfect for a grilled cheese sandwich. 

Hawaiian Cheese

Pairing pineapple with cheese creates almost a charcuterie like sandwich. Charcuteries are usually a combination of dried meats, cheeses, fruits and other nibbles. So, creating this type of sandwich with crispy grilled bread is the perfect combination. 

Pineapple and Cheese

Pineapple has lots of health benefits. It contains a digestive enzyme called bromelain. This has anti-inflammatory and pain-relieving properties. 

It’s kind of nice to know that with this delicious sandwich you’re getting some great health benefits. Pineapple’s loaded with vitamin C and that also helps keep inflammation levels low. 

Pineapple Cheese Sandwich

Nothing’s better than a grilled cheese and when you pair with the melted cheese and crispy buttered bread the pineapple, then great things happen. Another great part of this sandwich is the addition of the greens. While I used arugula, you could use baby spinach. Those would be my two favorite choices. 

Cheese Pineapple Sandwich

You can certainly use fresh pineapple with this sandwich, too. 

Cutting into smaller tidbit sizes might work better for both grilling and for eating. Small bites of the sweet pineapple will compliment the sandwich well. 

Hawaiian Grilled Cheese

Another thing that makes this grilled cheese even more luscious. The cream cheese you’re using. And, it’s got to be whipped. Yes, the whipped has this airy creamy texture that is like warm marshmallows. 

Caramelized Pineapple Grilled Cheese

Nothing fills the belly like a good ol’ grilled cheese. If you’re looking for more ideas, then here are some options. 

Goat Cheese Hippie Grilled Cheese

Pomegranate Grilled Cheese

Pepperoni Grilled Cheese

caribbean grilled double cheese sandwich

caribbean grilled double cheese sandwich

Caribbean Grilled Double Cheese Sandwich

Yield: One Sandwich!

This Caribbean grilled double cheese sandwich is something that you'd never expect to taste when you bite into it!


  • 2 Dole Sunshine Sliced Pineapples, drained and more moisture patted out with paper towels
  • 1/16 (or large pinch) sea salt
  • 1/8 tsp. coarse ground pepper
  • 2 slices sourdough bread, artisan style preferred, sliced about ½ to ¾” thick
  • 3 Tbl. butter, salted, room temperature for easy spreading
  • 2 slices pepperjack cheese
  • 2 slices sharp cheddar cheese
  • 1/3 cup fresh spinach and arugula greens
  • 3 Tbl. whipped cream cheese, optional


Sprinkle the salt and pepper on the pineapple slice.

Heat a large cast iron skillet on medium high heat. Let it get hot. Put one tablespoon of butter in the skillet and the pineapples. Grill on each side about 75 seconds. Remove to a plate

Reduce heat to medium low.

Butter one side of each slice of bread. Start building the sandwich to grill.

On the unbuttered side of one slice, put the pepperjack cheese slices. Add the seared pineapple slices. Add the cheddar cheese slices. Top with the greens.

Put the whipped cream cheese on the unbuttered side of the top slice of bread (yes, your hand will get some butter on it from the other side). Place the whipped cream side on top of the greens (this will ‘glue’ the greens in place, too).

Cover the sandwich with a lid for about 60-75 seconds or until golden brown on the bottom side.

Carefully flip the sandwich with a spatula. Press down gently with a somewhat flexible egg flipper. Cover with the lid for about 60-90 seconds or until the bottom bread is crispy golden brown.

Optional: Add more arugula greens to the sandwich by stuffing in/around the sandwich.

Remove to a cutting board. Slice at an angle. Serve immediately.


If you want to add a protein like deli sliced smoked ham, turkey or another meat, that’s also an option. Fold over the meat slices and place on top the cream cheese when grilling.

Your sharing is GOLDEN! Thank you!

Your sharing and comments help me stay in business! Share a photo if you make the recipe #allyskitchen Thank you! xo Ally

caribbean grilled double cheese sandwich

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  1. What in tarnation did I just read? Is this post a joke? (The actual post, not necessarily the recipe). I’m so confused.

    1. Hi, Maggie…first of all, it’s good to hear the word ‘tarnation’…haven’t heard that in years! Thanks so very much…not sure how this happened but I’m working on it. Appreciate you! And, the recipe’s really great! ~ally

  2. This sounds amazing, Ally! Love that melted cheesy deliciousness, and the greens go beautifully with it all. YUM!

    1. Thank you, sweet Michele!! It’s one of those sandwiches that is truly a treat and that only comes rarely b/c it’s just so decadent!! xo

  3. I love grilled pineapple and I love grilled cheese! Together the two would be heaven which I am feeling like right now!

    1. Thank you, Abbe…yeah, pineapple and grilled cheese go together like a PBJ! xoxo

  4. Christine says:

    I can see myself eating this sandwich. Looks so good! Yum!

    1. Thanks, Christine…it’s gooeeey ooooeeee good!!

    1. Thank you, dear Mary…it’s one of those ‘only on special occasions’ sandwiches b/c it’s just so darn decadent!!

  5. Dear Ally, you have always secret ingredients in your recipes, maybe one day you should consider opening a restaurant and open the door to those creative ideas, and let people enjoy the food! I am pretty sure you will do miracles – just a suggestion! Love the caribbean grilled double cheese sandwich.

    1. Only only if you come and help me run it!! Thank you, Hadia! Oh, that restaurant business is brutal…maybe in my next life!! You’re the sweetest! xoxo

    1. My Dear Ann!!! Thank you, luv…it’s really good and just so dang simple!! xox

  6. Oh Ally this is so Tropical I love that pineapple is on this and cheese holy moly what an amazing sammy! Thanks!

    1. Claudia! This is soooooooooooo good…thank you!! You just want to start dancing w/each bite!! xo ~ally

    1. Awwhhhh, thank you, luv! I must say it’s got all the ‘it’ factor going on!! xo ~ally

  7. OMG! This sounds so YUMMY!

    1. Robin!! Thanks, luv! Think you and Steve might likeee! Sure do miss y’all…when you coming back to the ‘hood??? xoxox

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