1 Whole Pineapple
2 Tablespoons brown sugar (optional)
A cutting board and knife
A really big skewer
A hardwood lump charcoal fire, or wood fire. Chemically-bound briquettes or a gas grill can give an off-taste, but real smoke is always tasty.
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Step 1: Prep the Pineapple
Lay the pineapple flat on a cutting board. Slice the top and bottom off, then set upright and slice the remaining skin off.
You can choose to rub the 2 tablespoons of brown sugar over the pineapple at this point, or not. I find that brown sugar doesn't make much of a taste difference -- roasting alone brings out the sweet-tangy goodness of pineapple. The sugar does help the pineapple get soft all the way through, though. I keep doing it both ways.
If you're going to be building your fire somewhere other than home, you can prep the pineapple ahead of time, cover it with plastic wrap, and stick it in a cooler. The brown sugar will start dissolving into the pineapple and get all sticky/syrupy, so if you want to make sure it doesn't leak at all, use a large plastic zip-top bag.
Step 2: Skewer the Pineapple
You need a skewer big enough to hold the weight of a pineapple. I have great churrasco skewers from Brazil, but if that's not available to you, you might be able to repurpose a rotisserie skewer or another item. Just make sure it can hold the weight of the pineapple. Skewer the pineapple straight through its woody core.
Step 3: Roast the Pineapple
After you have some nice coals built up, put the pineapple nearby, but not too close. It will depend on the heat of your fire, but you want it about ten inches away. If it starts to brown/blacken quickly, get it further away. Here, I didn't have enough vertical space, so I set the pineapple to the side of my coals. Fiddle and turn the pineapple as often as you like. It should take at least half an hour to roast the pineapple. Much quicker than that, and it will be cold and hard on the inside.
Step 4: Slice and Eat!
Remove your roasted pineapple from the skewer. Avoiding the woody core, slice off slabs of pineapple. These can be further cut into bite-sized or at least finger-food sized pieces. Enjoy it while it's hot!