/ / / caribbean grilled double cheese sandwich

caribbean grilled double cheese sandwich

Dole Signature Recipes | Dole Signature Recipes | Sandwiches
caribbean grilled double cheese sandwich
Print Friendly, PDF & Email

Thanks to Dole Sunshine for partnering with me for this post! I am the creator of this recipe and for the description and information that follows. For a full disclosure, click here!

When you think of comfort food, what comes to mind? Mashed potatoes. Chicken soup. Pizza. Pasta. Certainly in that category is the grilled cheese sandwich. And, this caribbean grilled double cheese sandwich is something that you’d never expect to taste when you bite into it!

Taste Testing the Grilled Cheese

I have the privilege of doing cooking demos at ‘Live on Green’ in Pasadena, California. Live on Green is a three-day festival for families and children leading up to the iconic Rose Parade. There’s always so much to do, exhibits, face paintings, demonstrations, and every year the United States Air Force has been there. Young airmen, officers, and more all decked out in their fatigues or dress uniforms. Now, guess who gets to be taste testers at the cooking demos? Yep, these wonderful young men and women!

So, when this sandwich was made, it was served to a young Lieutenant. The runner took it hot from the grill where I was cooking on stage. The sandwich was simply perfect. So easy to make. And, everyone was really wondering, yes, you could see the look of confusion on their faces, how it would taste because in this sandwich were two caramelized grilled pineapple slices! Yes, a surprise ingredient sharing the buttery grilled sour dough bread and ooooeeee gooooeeee melted cheeses that would be unexpected!

Well, you should have seen the crowd as the sandwich was served. Everyone turned almost simultaneously in their chairs to look straight at the young man sitting off to the side with the other two taste testers. He took the sandwich. Picked up one half of it. Took a big healthy bite. Seconds passed. Chewing chewing. No words. And, then the MC said, ‘So how do you like it?’ His response, and I kid you not, was simply ‘OMG, OMG, OMG!’ Then he said, ‘It’s soooooooooo good and I never thought to put a pineapple on it!’ Yes, the young military man devoured the entire sandwich. And, yes, I had to make two more for the other two taste testers! Now, if that’s not enough convincing for you to try this recipe, then you’re gonna be missing a divine culinary experience!

Hey, have you ever had Dill PIckle Chicken? Well, check it out!

caribbean grilled double cheese sandwich

Yield: One Sandwich!

caribbean grilled double cheese sandwich


  • 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


  1. Sprinkle the salt and pepper on the pineapple slice.
  2. 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
  3. Reduce heat to medium low.
  4. Butter one side of each slice of bread. Start building the sandwich to grill.
  5. 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.
  6. 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).
  7. Cover the sandwich with a lid for about 60-75 seconds or until golden brown on the bottom side.
  8. 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.
  9. Optional: Add more arugula greens to the sandwich by stuffing in/around the sandwich.
  10. 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

Similar Posts


  1. 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

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

  2. 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!!

  3. 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

  4. 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

  5. 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

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.