Hold the pineapple upright and slice sections from top to bottom, each about six inches long. Then slice those sections into inch wide spears, about 11-12 in all.
Cut 11-12 strips of bacon in half and arrange on parchment or aluminum foil lined shallow baking dish (or cookie tray with sides).
Bake the 22-24 bacon pieces at 375 degrees for ten minutes only and remove from oven.
The partially cooked bacon pieces will shrink a bit, but should still be long enough to wrap once around the pineapple.
Cut pineapple spears in half, about 3” long each.
Place brown sugar in a bowl and roll each pineapple spear in the sugar, lightly coating.
Line the bottom of a clean, shallow baking dish with parchment paper or aluminum foil.
Wrap one piece partially cooked bacon around one pineapple piece, tucking the bacon ends underneath the pineapple, then place in the clean baking dish, tucked ends on the bottom.
Repeat the wrapping process until all the bacon halves have been used.
Bake tray of bacon wrapped pineapple for an additional 10-15 minutes at 375 degrees until bacon is cooked all the way through, nicely browned.
Remove from cooking dish, drain if necessary, and place onto serving platter. Can be eaten warm or cold.
