How do I lick a plane?
Solution 1:
Here are video guides for every achievement in Goat Simulator. On the bottom of the page, you can find the "Mile High Club — Lick the Hanging Glider" achievement, which I think is the one you are looking for.
Same as you tried: you must climb up the big crane and then jump on the glider when it's close enough to lick it. It's the last video. Watch at 0:30 to see how to perform the jump to reach the glider.