Start by combining the brown sugar, melted unsalted butter, vanilla extract, and ground cinnamon in a small bowl. Mix it well until the brown sugar dissolves a bit into the butter, creating a luscious, fragrant marinade. Trust me; the aroma alone will have you drooling.

Take your ripe pineapple and slice it into long spears. Aim for about ½ inch thick. This thickness allows them to cook evenly on the grill while maintaining their juicy integrity. If you’ve never sliced a pineapple before, don’t worry! Slice off both ends, then stand it upright and slice down, removing the tough skin. Simple.

Place the pineapple spears in a large bowl and pour the marinade over them. Ensure each spear gets coated. Allow them to soak for at least 10 minutes. If you have time, letting them marinate for 30 minutes will amplify the flavors even more.

While the pineapple marinates, preheat your grill. Aim for medium-high heat. If you’re using a gas grill, this will be straightforward. If you're using charcoal, wait until the coals are covered in gray ash. A hot grill is essential for a good caramelization.

Once the grill is ready, place the marinated pineapple spears on the grate. Grill each side for about 3–4 minutes. You’re looking for nice grill marks and that beautiful caramelization. If you have a basting brush, brush on some extra marinade halfway through for an added sweet glaze.

Once grilled to perfection, remove the pineapple from the grill and let rest for a minute. Serve warm—perhaps with a sprinkle of freshly cracked black pepper for an unexpected kick. Enjoy as is, or ladle some vanilla ice cream over the top for an indulgent dessert.