Fire up the grill and target a surface temperature of 400 to 425 degrees Fahrenheit. If you are running charcoal, set up a two-zone fire with a hot direct side and a cooler indirect side. Let the grill preheat with the lid closed for at least 10 to 15 minutes so the grates are screaming hot. Proper grill temperature is the single most important factor in getting those deep, clean grill marks and triggering caramelization.

While the grill is heating up, prepare your pineapple. Lay it on its side on a sturdy cutting board and slice off the top and bottom. Stand it upright and cut away the skin in downward strips following the curve of the fruit. Slice into uniform rings approximately 1 inch thick. Thinner slices will burn before caramelizing properly, so do not go any less than three-quarters of an inch. Pat the rings dry with paper towels to remove excess surface moisture.

Mix the honey glaze. In a small bowl combine the raw honey, melted unsalted butter, ground cinnamon, ground ginger, cayenne pepper, kosher salt, fresh lime juice, and vanilla extract if using. Whisk everything together until smooth and fully incorporated. Set aside half the glaze for serving later and keep the other half for basting on the grill.

Clean your grill grates with a wire brush and then oil them using a folded paper towel dipped in high smoke-point oil like canola or avocado oil, held with long tongs. This prevents sticking and helps develop those picture-perfect char marks. Place the pineapple rings directly over the hot zone of your grill in a single layer with no overlapping.

Grill the pineapple rings over direct heat for 3 to 4 minutes without moving them. Resist the urge to shift them around. Let the grill do the work. You will know they are ready to flip when the rings release naturally from the grates and you can see deep golden-brown char marks forming on the contact side. Use long tongs to flip each ring carefully.

After flipping, grill the second side for another 3 to 4 minutes over direct heat. During this final stage, brush the top caramelized side generously with your honey glaze using a basting brush. Apply it in a thin, even coat and let it set on the fruit for 60 to 90 seconds. Then flip one more time for just 30 to 45 seconds so the glaze side faces the heat and tightens into a lacquered finish. Watch it closely because honey burns fast over a hot fire.

Pull the pineapple rings off the grill and let them rest on a clean cutting board or serving platter for 2 to 3 minutes. Just like you rest the meat after a long cook, giving the pineapple a brief rest allows the internal juices and caramelized sugars to redistribute and settle. Drizzle with the reserved honey glaze right before serving for a fresh glossy finish.

Serve the grilled pineapple hot off the grill as a standalone dessert topped with vanilla ice cream, a side dish alongside grilled pork or chicken, or sliced into chunks as a burger or taco topping. Garnish with a sprinkle of flaky sea salt, a dusting of extra cinnamon, or fresh mint leaves for a pop of color. Any leftover rings store well in an airtight container in the refrigerator for up to 3 days.