Here is the full list of all 16 Pineapple on pizza achievements. It takes around 0-1 hour to unlock all of the achievements on Windows.
Get out of the island.
Ruin the limbo.
Approach the bench.
Approach the kids playing.
Jump from the cliff.
Approach the cliff.
Approach the skilled dancer.
Approach the turtle.
Step inside the circle.
Approach the baby.
Activate the volcano.
Approach the man feeding the birds.
Walk through the corn plantations.
Step onto a sailboat.
Approach the statue.
Play.