Select a pineapple with a golden-yellow exterior and slight give when squeezed—this indicates peak ripeness and maximum natural sugars that caramelize beautifully on the grill.

Cut pineapple into 3/4-inch thick slices to prevent burning while ensuring the interior cooks through and develops caramelized edges without drying out.

Use paper towels to remove excess moisture from pineapple slices before grilling—this promotes better caramelization and prevents steaming on the grill grates.

Lightly brush slices with a mixture of butter and brown sugar, or sprinkle cinnamon sugar before grilling to enhance natural sweetness and create a crispy, caramelized crust.

Grill each side for 3-4 minutes without moving the slices, allowing deep caramelization and grill marks to develop before flipping once for optimal flavor and presentation.