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.
Approach the kids playing.
Approach the statue.
Approach the bench.
Step inside the circle.
Approach the skilled dancer.
Step onto a sailboat.
Jump from the cliff.
Approach the cliff.
Approach the baby.
Activate the volcano.
Approach the turtle.
Approach the man feeding the birds.
Walk through the corn plantations.
Ruin the limbo.
Play.