Prep the pineapple: Slice off the top and bottom.
Stand it upright and cut away the skin. Slice into rounds or spears. Remove the core if you prefer softer bites.
Make the glaze: In a small bowl, mix brown sugar, honey (or maple), cinnamon, vanilla, and a pinch of salt.
It should be thick but brushable.
Heat the grill: Preheat to medium-high (about 400–425°F). Lightly oil the grates or your grill pan to prevent sticking.
Brush and grill: Brush one side of the pineapple with the glaze. Place glazed-side down on the grill.
Cook 3–4 minutes until grill marks form.
Flip and finish: Brush the top with more glaze, flip, and grill another 2–4 minutes until caramelized and tender at the edges.
Serve warm: Plate the pineapple and add your toppings—ice cream, coconut cream, toasted coconut, mint, or a squeeze of lime.