Prepare a grill for direct and indirect heat: For gas grills (with 3 or more burners), turn all the burners to medium-high heat; after about 15 minutes turn off one of the side burners and turn the remaining burners down to medium. For charcoal grills, bank one chimney starter-full of lit and ashed-over charcoal briquettes to one side of the grill. Set up a drip pan on the other side to avoid flare-ups. (Be sure to consult the grill manufacturer's guide for best results.)
Grill the pineapple over direct heat until golden on both sides, about 5 minutes per side. Let cool 5 minutes, then place on the cut side of one of the cheese halves. Place the other piece of cheese on top with the cut side touching the pineapple. Lay the prosciutto slices out on a work surface so they overlap in the middle and look like the spokes of a wheel. Put the cheese and pineapple round in the middle of the prosciutto and bring up one slice at a time to cover. The cheese and pineapple should be fully wrapped in prosciutto.
Grill over direct heat until starting to turn golden and crisp, about 3 minutes. Flip with a spatula and cook until golden and crisp on the other side, about 3 minutes. Move to indirect heat and cover the grill. Cook until hot throughout and gooey, 5 to 8 minutes more depending on your grill. Serve immediately with crackers and bread.
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