This is attainable in Goat Ville. Having the Angel Goat and Double Jump mutators turned on will allow you to navigate more easily, so they are recommended.
Make your way to the construction site, and next to the street you'll see some blue and red containers. Double jump onto the red containers then double jump onto the roof right next to them. You will see four fans on this roof. Now your goal is to jump onto a fan and allow it to shoot you up into the sky. As soon as you are shot up, press
to ragdoll, then go for all five trampolines in one combo, without landing or using the same one twice. Make sure as you ascend you avoid the crane as it can screw you up.
1. At the top of the construction site
2. Upper level of the swimming pool
3. Lower level of the swimming pool
4. On the grass between a blue house and red house
5. Across the street in the fenced-in area of the house where you originally spawned
It helps to adjust the camera so you are looking at the ground. Use
to aim for the trampolines and
to adjust the camera. Once you hit the fifth one, the achievement will unlock.