You can earn this trophy as early as Chapter 2.
In Chapter 2, Mike will task you to steal a car from a rough part of town. (Vito and Joe talk about how awful the place is)
After stealing the car you'll follow the waypoint back to Mike's. But on the way you'll come to a slopped road that leads into a tunnel. If you get enough speed down the road you can get some air off the part of the road that dips.
Here is a clip I made for example :)
https://www.trueachievements.com/gameclip.aspx?clipid=154749...