Pilotwings Resort contains two modes of play. The first, "Free Flight Mode", allows the player to freely explore Wuhu Island using any type of aircraft they have unlocked. Various collectibles such as balloons and stunt rings can be picked up to unlock certain features in the game, like diorama statues and the player's very own castle on the archipelago's private island. In this mode, there is a time limit which is extended for the next playthrough when the player has collected a set number of balloons. The second, "Mission Mode", requires the player to complete a series of objectives within certain parameters. These increasingly difficult missions span Training, Bronze, Silver, Gold, Platinum and Diamond classes (the former only being unlocked after achieving a three star rank on every mission). The player is graded between one and three stars on their performance in each mission. When players achieve higher star rankings, they grow closer to unlocking several in-game bonuses, including a "Meca Hawk" robot from Pilotwings 64 that walks around Wedge Island and alternate credits. The basic aircraft are plane, rocket belt, and hang glider. As players progress through Mission Mode, they unlock the "Super Vehicles," consisting of the turbo jet, super rocket belt, and pedal glider. Each holds its advantages, like the turbo jet being able to fly at high speeds, but each is more difficult to control. The Super Vehicles are all featured in their own finales in the Diamond Class missions. A flying squirrel suit is also available in the game, but it is not an unlockable vehicle and only appears in one mission.
The game was released on March 25, 2011 in Europe, on March 27, 2011 in North America, on April 14, 2011 in Japan and on April 14, 2011 in Australia.
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