This dessert comes from the book How To Grill: The Complete Illustrated Book of Barbecue Techniques by Steven Raichlen. It's really a grilling recipe, but you can do it on the WSM if you have a lot of hot coals leftover at the end of a cooking session.
As always...click on any of the pictures to view a larger image.
Choosing A Pineapple
Pineapples do not ripen and get sweeter after they're picked from the plant they grow on (Photo 1), so it's important to choose a good pineapple at the grocery store. According to the Hawaii Department of Agriculture, here's what you should look for:
I prefer the hybrid "Super Sweet' or "Golden" varieties. When choosing a hybrid pineapple, my experience is that those with the sweetest, most fragrant smell tend to taste the sweetest.
Prepping The Pineapple
Twist off the green crown, rinse the pineapple, and pat it dry. Cut off the top and bottom, then cut off the shell in strips, using a sawing motion with a very sharp knife.
Cut the pineapple into 1/2" slices, then remove the core from each slice using a tablespoon measure or a melon baller.
Sugar-Coating The Slices
Here are the ingredients you'll need to coat the pineapple slices.
Combine the sugar and cinnamon, mixing well. Place the coconut milk and the sugar mixture into separate baking dishes. Place a pineapple slice in the coconut milk, coating both sides, shake off the excess, then dredge the slice in the sugar mixture.
The slices will have a thick coating of sugar on both sides. Don't worry, much of that sugar will melt away during grilling.
As an alternative to coconut milk, brush the slices with melted, unsalted butter instead. I did 3 slices with coconut milk and 3 slices with butter.
Grilling The Slices
Put the cooking grate directly on top of the charcoal chamber in the charcoal bowl. Make sure you still have lots of hot coals in the bowl before grilling the pineapple. You may need to stir the coals to dislodge the ashes, which should really get those coals fired up.
Arrange the slices on the grate and grill for 4-6 minutes on each side until nicely caramelized. The melting sugar may flare-up when it hits the hot coals, so pay close attention to the fire.
Serve warm as-is, or with a scoop of vanilla ice cream.
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