This is a story-related trophy and cannot be missed via normal campaign progression.
When you jump out of the plane, do NOT
deploy your wing suit. Instead you will fall into the ocean and unlock the "Free Fall
" trophy (if you already have, you can skip this part and deploy your wing suit).
You will fail the mission and will restart where you jump off the plane. On your second dive attempt, deploy the suit and glide onto the second island to pop the trophy.