Combatants fight atop the wings of a biplane as it flies through rings in the sky over a flat, 2D island. The top wings of the biplane serve as soft platforms, while the bottom wings are semisoft. The cockpit in the middle is a solid wall, splitting the lower half of the stage in two. The stage tilts as the plane makes turns in the air.
After some time, the fighters will be dropped onto a yellow monoplane which flies towards and over Wuhu Island. The wings of this plane form a semisoft platform. The rotors below the wings can be stood on, but this is risky to attempt, as their edges cannot be grabbed. When players are launched, they may rebound off the terrain off the island, which may KO them but can also save them when they would otherwise have continued past the blast line. Miis can be seen flying with Rocket Belts from Pilotwings Resort.
The yellow plane will eventually make its way back to the first island and drop players onto the red biplane, starting the loop over again.
The Omega form is set on a floating platform with the color scheme of the yellow plane which appears to have a design of aircraft structure at the bottom. Like Wuhu Island the stage tours the same area but take a different path. The planes can still be seen in the background.
Pilotwings is banned in tournaments due to powerful camping spots on both planes, especially the yellow plane's rotors, as well as due to KOs being caused or prevented by the damaging terrain and tilting of the planes. The planes can also impact a character trying to recover, as they can tilt at the wrong moment.
As a stage named after its series, it originates from both Pilotwings for the SNES and Pilotwings Resort for the 3DS. The red biplane in this stage is the 'Light Plane' used in Pilotwings, and the flat, 2D island is the runway from lesson 3 of Pilotwings. The island is also in lesson 7, however, lesson 3 takes place in the daytime, while lesson 7 takes place at sunset. The yellow plane is modeled after the mono-wing sea planes used in Pilotwings Resort as it flies towards Wuhu Island. Wuhu Island first appeared in Wii Fit and Wii Sports Resort, and is also the main area in Pilotwings Resort. It also appeared in Mario Kart 7 as a track in the game.