This sandwich has been a backyard staple for my family ever since a summer barbecue introduced me to the magic of grilled chicken paired with caramelized pineapple. I first tried this combination when I wanted something that felt festive but was simple enough to pull together on a busy weeknight. The bright, slightly acidic pineapple juice softens and sweetens the chicken while the soy-brown sugar marinade gives the meat a subtle glaze when it hits the grates. The contrast between the juicy grilled chicken, melted provolone, and a warm pineapple ring is unexpectedly comforting and bright at the same time.

I remember the first time I served these to my skeptical teenager: one bite and the request for seconds came immediately. The flavors are familiar—sweet, salty, tangy—but assembled in a handheld form that feels celebratory without fuss. These are ideal for a summer lunch, an easy dinner, or a poolside meal. With a short active prep time and an overnight soak for flavor, you can let the marinade do the heavy lifting while you plan sides or relax with guests.

Ingredients

• Chicken: 2 boneless, skinless chicken breasts (6 ounces each) sliced to make four thin cutlets. Choose fresh, even-thickness breasts or trim and pound to 1 inch for even cooking; larger breasts will benefit from pounding.
• Seasoning: 1/2 teaspoon coarse salt, 1/4 teaspoon black pepper, 1/4 teaspoon garlic powder. These simple seasonings enhance the marinade without overpowering the pineapple notes.
• Pineapple: 1 8-ounce can pineapple rings or 4 fresh rings, patted dry. Canned juice becomes the base of the marinade; fresh pineapple gives slightly brighter fruit flavor and firmer rings.
• Marinade: 2 tablespoons low-sodium soy sauce, 2 tablespoons packed brown sugar, 2 teaspoons Dijon mustard plus the pineapple juice. The balance of sweet and salty helps caramelize the surface during grilling.
• Cheese: 4 slices provolone cheese. Provolone melts evenly and adds a mild creaminess that complements the fruitiness.
• Buns: 4 buns or kaiser rolls, toasted if you like texture contrast. For a gourmet touch pick brioche or potato rolls.
• Condiment: 1/4 cup mayonnaise. Spread thinly on buns for moisture and richness; swap for aioli or Greek yogurt for variation.

Instructions

Prepare the chicken: Pound the chicken breasts to an even 1-inch thickness if needed. Slice each breast in half to yield four pieces about 4 to 5 ounces each. Season both sides with the salt, pepper, and garlic powder; this step ensures the exterior has seasoning to build flavor when grilled. Make the marinade: Combine the canned pineapple juice (reserve the rings for grilling), soy sauce, brown sugar, and Dijon mustard in a bowl. Whisk until the sugar dissolves. Place the chicken in a shallow dish or zip-top bag and pour the marinade over it, turning to coat. Refrigerate at least 12 hours for best flavor; overnight allows the pineapple enzymes to subtly tenderize the meat. Preheat the grill: Heat the grill to medium-high and oil the grates well to prevent sticking. Use tongs and a folded paper towel dipped in oil to grease grates, or brush with a high smoke-point oil. A temperature around 400°F is ideal for direct grilling and caramelization. Grill the chicken: Remove chicken from the marinade and let excess drip off. Grill for 12 to 15 minutes total, flipping once halfway through; check for an internal temperature of 165°F with an instant-read thermometer. Look for a nicely charred exterior and clear juices. Add the cheese: With about 3 minutes remaining on the grill, place a slice of provolone over each piece of chicken so it melts gently while the meat finishes cooking. Grill the pineapple: Place the pineapple rings on the grill while the chicken cooks—about halfway through the chicken’s cook time. Turn once to get even caramelization and grill marks, roughly 2 to 3 minutes per side depending on heat. Assemble: Smear mayonnaise on both bun halves. Place the melted-cheese-covered chicken on the roll and top with a warm pineapple ring. Serve immediately so cheese remains gooey and pineapple is warm.

Storage Tips

Store leftover chicken and pineapple separately in airtight containers in the refrigerator for up to three days. Keep buns at room temperature in a sealed bag to avoid refrigeration that makes them stale faster. For longer storage, freeze cooked chicken in a single layer on a sheet pan, then transfer to freezer bags; label with date and defrost overnight in the refrigerator before reheating gently on the grill or in a skillet to preserve moisture. Reheat pineapple briefly on the grill or in a hot skillet for a minute per side to revive caramelization.

Ingredient Substitutions

Swap provolone for Swiss or Monterey Jack for similar melt and mild flavor. Use tamari instead of soy sauce for a gluten-free option, and choose dairy-free cheese plus vegan mayonnaise to make the sandwich dairy-free. Replace brown sugar with maple syrup for a different caramel note—reduce quantity to 1 tablespoon to avoid excess liquid. If fresh pineapple is in season, use it for firmer texture and brighter flavor; cut rings from a ripe pineapple and pat dry before grilling.

Serving Suggestions

Serve alongside a crisp coleslaw, a simple green salad with citrus vinaigrette, or sweet potato fries for a balanced plate. Garnish with thinly sliced red onion or a handful of arugula for peppery contrast. For a party, make a sandwich bar with different cheeses, sauces such as sriracha mayo or teriyaki glaze, and toasted sesame seeds so guests personalize their sandwiches. Pair with a cold lager or an iced tea with lemon for a quintessential summer pairing.

Cultural Background

The idea of combining grilled meats with pineapple is most commonly associated with Hawaiian-inspired cuisine, where the tropical fruit is a prominent flavor. While not an authentic indigenous Hawaiian preparation, pineapple found its way into a range of island-influenced dishes due to historical trade and plantation-era agriculture. The sweet-savory approach reflects broader Polynesian and Pacific Rim influences where fruit and meat pairings are common. Over time, this flavor combination filtered into American backyard cookouts as an accessible, festive pairing.

Seasonal Adaptations

In summer use fresh, sweet pineapple for firmer rings and brighter acidity. For winter or when fresh fruit is less available, canned rings work well and provide consistent sweetness. In colder months consider warming the sandwich with a smear of grainy mustard and caramelized onions to add depth. For a holiday twist, glaze the pineapple with a little molasses and add smoked paprika to the marinade for a bolder profile.

Meal Prep Tips

Marinate chicken overnight in a shallow container or zip-top bag to maximize surface contact. On cook day, preheat the grill and have pineapple and buns ready so nothing sits too long. For weekly meal prep, grill all chicken at once and store individual portions in meal containers with a separate compartment for pineapple and bun. Reheat gently in a skillet with a splash of water and a tight lid to restore moisture, then assemble fresh to keep textures vibrant.

These sandwiches are a joyful blend of easy technique and bold flavor—perfect for simple family dinners or when you want a sandwich that feels like a celebration. Give the marinade time, treat the grill with respect, and enjoy the fuss-free tropical lift this brings to the table.