This brown sugar grilled pineapple has been a small but reliable star of my summer cookouts for years. I first discovered this combination the summer I wanted a simple, no-fuss dessert that could stand up to smoky burgers and charred corn; the result was unexpectedly celebratory. The exterior caramelizes into ribbons of sticky, golden glaze while the interior stays juicy and bright. Each bite balances sweet and tang, the hint of vanilla rounds the flavor, and the whisper of cayenne keeps the finish lively. It’s one of those dishes that makes people say, "I didn’t know grilled fruit could taste this good."

I love that this preparation is quick to assemble but rewards patience in the marinating. Letting the pineapple rest in the brown sugar-vanilla mixture for at least 30 minutes — or overnight if you plan ahead — draws out pineapple juice and dissolves the sugar into a natural syrup that becomes the finishing drizzle. It’s perfect as a simple dessert, a colorful component for plated entrees, or a bright side for heavier grilled meats. I often prepare extra to spoon over vanilla ice cream or to fold into a summer salad with arugula and toasted almonds.

Ingredients

• Fresh pineapple (1 whole): Choose a ripe pineapple with a sweet aroma at the base, firm skin with a little give, and bright green leaves. If you prefer convenience, buy a pre-peeled, cored pineapple from the produce counter. For this recipe you’ll peel, core, and cut into 8 spears.
• Light brown sugar (1/4 cup): Provides the caramel flavor and sticky glaze when heated. I use light brown sugar for a milder molasses note; dark brown will deepen the flavor if you prefer a richer caramel note.
• Cayenne pepper (1/4 teaspoon): A very small pinch adds a warm background lift without heat that competes with the sweetness — adjust to taste.
• Vanilla extract (1 teaspoon): Adds aromatic sweetness and rounds the glaze. Pure vanilla extract delivers the best flavor; imitation still works in a pinch.
• Kosher salt (1/8 teaspoon): Balances the sweetness and enhances the pineapple’s natural acidity.
• Vegetable oil spray: A light coating on the grill pan prevents sticking and helps achieve even grill marks. You can substitute an oil brush with neutral oil if you prefer.

Instructions

Prepare the pineapple: Peel, core, and cut the pineapple into 8 evenly sized spears. Even thickness helps them grill evenly and prevents thinner pieces from falling apart. Place the spears in a large mixing bowl so they sit in a single layer when possible. Make the glaze and toss: Sprinkle 1/4 cup light brown sugar, 1/4 teaspoon cayenne, 1 teaspoon vanilla extract, and 1/8 teaspoon kosher salt over the pineapple. Gently toss until each spear is lightly coated. The sugar will draw out juice and begin dissolving; you should see a few tablespoons of liquid collect in the bottom of the bowl. Do not discard this flavorful liquid. Marinate: Cover the bowl with plastic wrap and let sit at room temperature for 30 minutes. The sugar will mingle with pineapple juice to form a thin syrup; marinating at room temperature intensifies flavor, but you may refrigerate and marinate overnight for a deeper infusion. Preheat the grill pan: Heat an indoor grill pan over high heat until very hot, about 3 to 5 minutes. Spray the pan lightly with vegetable oil spray just before adding the pineapple to prevent sticking and to get clean grill marks. Grill the pineapple: Place spears on the hot grill pan and cook 1 to 2 minutes per side until you see caramelized grill marks and the sugar glaze is bubbling and sticky. Use tongs to rotate; avoid pressing or piercing the fruit so it retains its juices. Syrup finish: While the pineapple is grilling, pour the reserved marinade liquid into a microwave-safe bowl and heat on high for 90 seconds or until it becomes bubbly and slightly syrupy. Alternatively, simmer gently on the stovetop until reduced by a third. Drizzle this warm syrup over the grilled pineapple just before serving.

Storage Tips

Leftover grilled pineapple keeps best in the refrigerator in a sealed container for up to 3 days. To retain the best texture, allow the fruit to cool to room temperature before sealing; trapping steam accelerates sogginess. For longer storage, freeze spears on a baking sheet until solid, then pack in a freezer bag for up to 3 months. Reheat gently on a hot grill pan for 30 to 60 seconds per side or warm in a 350°F (175°C) oven for 5 to 8 minutes to reintroduce caramelization without turning the fruit mushy.

Ingredient Substitutions

If you don’t have light brown sugar, mix 2 tablespoons of granulated sugar with 1 tablespoon of molasses to mimic its flavor. Swap cayenne for a pinch of ground ginger for a warmer, spicier note that complements pineapple’s acidity. If vanilla isn’t on hand, a splash (1/2 teaspoon) of rum or a touch of orange zest brightens the profile. For a lower-sugar option, reduce the brown sugar to 2 tablespoons and increase marinating time slightly to let the fruit’s own juices do more of the work.

Serving Suggestions

Serve warm with a scoop of vanilla ice cream and a drizzle of the reserved syrup for an effortless dessert. For savory pairing, offer alongside grilled pork chops or jerk chicken — the sweetness cuts through richness and the charred notes echo the grill. For brunch, chop the grilled pineapple and fold into Greek yogurt with toasted coconut and macadamia nuts. Garnish with fresh mint or a squeeze of lime to add brightness and color.

Cultural Background

Grilling fruit is a simple technique used across many tropical and Southern cuisines to intensify natural sugars and introduce smoke. Pineapple itself has a long history of celebration in the Americas and Europe as a symbol of hospitality. Caramelizing pineapple with sugar is a modern adaptation that borrows from caramel and brûlée traditions, while adding warm spices like cayenne nods to Caribbean flavor pairings where pineapple is commonly grilled and paired with chilies or rum.

Seasonal Adaptations

In summer, use the ripest fresh pineapple available for maximum sweetness. In cooler months, consider roasting pineapple with a heavier brown sugar and butter glaze (if dairy is fine) to emulate the same caramelized effect in a hot oven. For holiday gatherings, serve grilled pineapple spears alongside spiced roasted meats and use holiday spices — cinnamon or star anise — in the glaze for a festive twist.

Meal Prep Tips

To save time, peel and core the pineapple the night before and store spears in the marinade in the refrigerator. If you marinate overnight, bring the bowl to room temperature for 20 minutes before grilling to avoid cold centers. Pack grilled spears in individual meal containers with a small sealed cup of syrup to reheat briefly in the microwave or on a grill pan just before serving for best texture.

Ultimately, this brown sugar grilled pineapple is proof that simple techniques and quality ingredients create memorable dishes. Whether you toss it on the grill for a weeknight treat or save it for a special gathering, it’s an easy way to add sweetness, acidity, and a touch of drama to any meal.