This brown sugar grilled pineapple has been a summer staple in my house ever since I first discovered how much a simple glaze can transform a humble fruit. I found this combination on an impromptu afternoon when a too-ripe pineapple was staring at me from the counter and the grill was already warm from cooking dinner. The result was unexpectedly luminous: the brown sugar melts into the pineapple's natural juices, creating a sticky, caramel-like coating while a whisper of cayenne lifts the sweetness. It became the happiest accident I ever served as dessert at an outdoor dinner party.

I love this version because it honors the pineapple's bright, tropical flavor while adding depth from the brown sugar and a little vanilla warmth. The texture coming off the grill is what keeps people reaching for more—charred edges that yield to a juicy, tender interior. My kids call it "caramel pineapple," and my friends ask for the recipe every time. It pairs as well with grilled meats as it does with a scoop of vanilla ice cream, which makes it one of the most versatile finishes for summer meals.

Ingredients

• Fresh pineapple: Choose a ripe, fragrant pineapple that gives slightly to pressure near the crown. Look for one with a sweet aroma at the base—Dole or Del Monte quality fruit is fine for most grocery stores. A ripe pineapple yields juicy, tender spears that caramelize well on the grill.
• Light brown sugar (1/4 cup): The light molasses in brown sugar deepens the caramel notes without overpowering the fruit. Use Domino or any store-brand packed brown sugar; measure by lightly scooping and leveling the cup.
• Cayenne pepper (1/4 teaspoon): A pinch of heat brightens the sweetness—use McCormick or a fresh grind. Reduce to 1/8 teaspoon for a milder profile, or leave out for children.
• Vanilla extract (1 teaspoon): Pure vanilla extract adds a warm, rich undertone. Nielsen-Massey or a good-quality pure vanilla makes a difference, but artificial vanilla will still give good flavor if that’s what you have.
• Kosher salt (1/8 teaspoon): A small amount enhances the pineapple’s natural sugars and balances the glaze—use Diamond Crystal or Morton, adjusting slightly if using fine table salt.
• Vegetable oil spray: Lightly oil the grill or grill pan just before adding the pineapple to prevent sticking and encourage even charring.

Instructions

Prepare the pineapple: Peel, core and cut one fresh pineapple into eight even spears. Aim for uniform thickness so the spears cook at the same rate—about 1 to 1 1/2 inches thick. If you buy a pre-peeled and cored pineapple, trim into spears carefully using a sharp chef’s knife on a sturdy cutting board. Make and toss with glaze: Place the pineapple spears in a large mixing bowl and sprinkle with 1/4 cup light brown sugar, 1/4 teaspoon cayenne pepper, 1 teaspoon vanilla extract, and 1/8 teaspoon kosher salt. Toss gently to coat, then you’ll notice several tablespoons of juice and sugar pooling—don’t discard it; that liquid will become the finishing syrup. Marinate: Cover the bowl with plastic wrap and let it sit at room temperature for 30 minutes so the sugar begins to dissolve and penetrate the fruit. For deeper flavor, refrigerate and marinate up to overnight—just bring to room temperature before grilling for even cooking. Preheat grill pan: Preheat a heavy grill pan over high heat until it’s smoking-hot; if using an outdoor grill, preheat to medium-high (about 425–450°F). Spray the pan or grates lightly with vegetable oil spray immediately before adding fruit to reduce sticking and encourage a clean sear. Grill the pineapple: Place spears on the hot grill and cook 1 to 2 minutes per side until you see dark char marks and the flesh softens slightly—do not overcook or the spears will turn mushy. Use tongs to turn gently and watch for the sugar to darken but not burn. Reduce the marinade to a syrup: While the pineapple cooks, pour the leftover marinade into a microwave-safe bowl and heat in 30-second increments for about 90 seconds total until it becomes bubbly and syrupy. Alternatively, simmer on the stovetop in a small saucepan over medium heat 2–3 minutes until slightly thickened. Serve: Transfer the pineapple to a serving platter and drizzle with the warm syrup just before serving. Serve immediately while warm and juicy.

Storage Tips

Store leftover grilled spears in an airtight container in the refrigerator for up to 3 days; keep the syrup separate if possible so the fruit maintains some texture. To reheat, briefly warm in a skillet over medium heat for 1–2 minutes per side or pop under the broiler for a minute to revive char. For freezing, flash-freeze grilled spears on a tray for 1 hour, then transfer to a freezer bag; thaw overnight in the fridge and rewarm gently to avoid sogginess. Quality indicators: if the fruit smells off or the texture becomes slimy, discard.

Ingredient Substitutions

If you don’t have light brown sugar, use the same amount of granulated sugar plus 1 teaspoon molasses for similar depth. For a lower-sugar option, swap half the brown sugar for a liquid sweetener like honey (use slightly less honey—about 3 tablespoons) and expect a slightly different gloss and flavor. Replace vanilla extract with rum or orange liqueur (1 teaspoon) for an adult twist. For spice swaps, smoked paprika can replace cayenne for a smoky warmth without heat, or add fresh grated ginger for a zesty lift.

Serving Suggestions

Serve warm with a scoop of vanilla ice cream, a dollop of Greek yogurt and toasted coconut, or alongside grilled pork chops for a sweet-savory contrast. For brunch, slice and layer over pancakes or waffles with a drizzle of the syrup. Garnish with finely chopped mint or lime zest to add color and a citrusy brightness. The spears also work well chopped into salads or salsa paired with cilantro and jalapeño for a lively side.

Cultural Background

Grilling fruit is a simple technique used in many culinary traditions—charring brings out natural sugars and adds a caramelized complexity. Pineapple itself has roots in South American and Caribbean cuisines, where it’s often paired with spicy or savory elements. The brown sugar glaze in this preparation mirrors Caribbean uses of brown sugar and spice to balance tropical fruit, while the grilling technique is widely embraced in American backyard cooking, making this dish a true cross-cultural favorite.

Seasonal Adaptations

In summer, use the sweetest, sun-warmed pineapple you can find and serve with fresh berries. In cooler months, warm the spears with cinnamon and a splash of rum in the glaze for a cozy flavor profile. For holiday grilling, sprinkle chopped toasted nuts over the finished pineapple or serve with a small spoonful of bourbon caramel for festive flair.

Meal Prep Tips

Marinate the pineapple a day ahead and keep refrigerated; when it’s time to cook, bring to room temperature for 20 minutes so it grills evenly. Prepare the syrup in advance and reheat gently when serving. Portion the spears into airtight containers for easy grab-and-go desserts or toppings. Use vacuum-sealed containers for longer freezer storage and label with date; defrost overnight in the refrigerator before reheating.

There is a special joy in serving something that looks and tastes like care with so little effort. Whether you share this at a backyard barbecue or a quiet dinner, it’s the kind of food that invites conversation and second helpings. Give it a try—you might find, as I did, that the simplest preparations often become family favorites.