Pineapple is one of the best fruits for grilling. It's high in sugar, which means it caramelizes beautifully over the high heat, such as that from a charcoal grill. It's super juicy, which means it won't dry out. And its large size and relatively uniform shape make it easy to cut into flat, grill-friendly slices. Also, its flesh is nice and firm, so it doesn't tend break apart while you're grilling it.
Why You Should Grill Pineapple
Grilling also produces grill marks where the pineapple slices meet the grill grate. This adds visual appeal and the way those marks turn a dark golden brown means that the sugars in the pineapple have caramelized, producing new and wonderfully complex flavors.
The best way to maximize the surface area that comes into contact with the grill is to slice the pineapple into horizontal coin-shaped disks.
However, slicing a pineapple this way means that each slice will have a section of the tough fibrous pineapple core at its center. The core is edible, but not especially palatable. Besides being tough and fibrous, it's less juicy and not as sweet as the outer parts of the pineapple. So realistically, any approach to serving pineapple, grilled or otherwise, has got to include removing the core.
Prepping the Pineapple
Prepping a pineapple for grilling means trimming the top and bottom, removing the skin, then slicing it and removing the core (although coring it can also be done before slicing it).
To remove the stem, lay the pineapple sideways on your cutting board and with a sharp chef's knife, simply cut straight down and across the top of the pineapple. Try not to remove any more of the fruit than you need to to remove the stem. Leave the pineapple on its side and cut off the bottom the same way.
Next, stand the pineapple up on your cutting board and remove the skin by cutting downward in a series of straight cuts along the outside. Again, try not to remove too much fruit, but you want to cut away all of the little eyes of the pineapple. You now have a cylinder-shaped pineapple that is ready for slicing and coring.
Slicing and Coring a Pineapple
Now it's time to slice your pineapple into individual round slices. Simply lay the pineapple on its side and use your chef's knife to cut across into slices about 1/2-inch thick. You can cut the core out of each individual slice using a paring knife, which isn't too laborious, and if you have decent knife skills it should turn out looking fine.
Another approach is to use a pineapple corer. Although a pineapple corer is extremely effective at removing the core of a pineapple, the way it does so is by a rotary motion which cuts the pineapple into one long continuous spiral, rather than individual slices. You can then use your knife to cut this long spiral into almost-rings. Because of the spiral shape, these sections may not lie perfectly flat on the grill, which is not ideal, but it'll basically be fine.
Note that you can cut your pineapple in half vertically (i.e. through the stem and core), and then in half again, to produce wedges, and then simply trim away the section of core at the tip of each wedge. Then just grill the wedges. This approach isn't appreciably easier than the pastry cutter approach (or even the paring knife technique), and results in portions of pineapple that, while tasty, lack the familiar ring shape characteristic of sliced pineapple.
Grilling the Pineapple
You can basically grill the pineapple over a medium-high grill (which is somewhere between 350 and 450 F) for 3 to 6 minutes or until nicely browned and slightly charred on one side, then flip with tongs and repeat.
However, you can also marinate the pineapple slices first. A simple marinade can consist of nothing but some brown sugar or a drizzle of honey, plus some Kosher salt, some bottled hot sauce, and a bit of extra virgin olive oil. Indeed, a light sprinkling of Kosher salt will help bring out even more sweetness in the pineapple.
Alternately, you could grill as-is and drizzle with a bit of honey or with a refreshing dipping sauce of yogurt or crème fraîche with lime juice and chopped mint leaves. But the truth is, grilled pineapple requires very little in the way of added flavors or toppings. Whether you're serving it on its own as a dessert or incorporating it in other dishes (think a slice of grilled pineapple on a burger), grilled pineapple is an easy and satisfying summertime treat.