Heat olive oil in a large nonstick pan.
Working in batches, cook the slices of bacon until fully cooked (if applicable), heated through, and pliable.
As you remove the slices from the pan, fold / roll each into a bite sized parcel, and secure with a toothpick - this will hold the shape as it cools.
Using a sharp knife, cut the top and bottom off the pineapple, then cut the rind / skin off. Cut into strips or slices, then into chunks.
Cut Provolone into 14 cubes, slice a thin piece off each bocconcini to allow it to sit flat.
Thread a piece of provolone onto a skewer, followed by a piece of pineapple.
Remove the toothpick from a slice of back bacon, thread it onto the skewer through the hole left by the toothpick.
Finally, stick the toothpick into a bocconcini ball, taking care to balance everything if you’ll be serving them upright (as shown).
Repeat with remaining ingredients.
Serve immediately, or cover and chill until ready to serve. Best when used within 2 days of assembling.