Willy Beamish is a kid who likes to goof off and have fun. Naturally, all the grown-ups get in the way by making him go to school, making him clean his room, etc. But now that's school's out for the summer, Willy is determined to have a good time and maybe even have his pet frog win the frog jumping contest. However Willy has a habit of getting into trouble, and naturally, that means it will be a challenge to get out of it.

The Adventures of Willy Beamish is a point-and-click graphical adventure. You play Willy Beamish, an eight-year-old kid who is just trying to get through life without losing his lunch money. But he'll have to deal with parents, teachers, babysitters, and bratty sisters. The player must solve different puzzles to ensure Willy can progress, get out of trouble and generally avoid ending up grounded.

The in-game time progresses even if no action is taken. This means many puzzles have to be solved in a certain time frame or rely on being in the right place at the right time. A special aspect of this game is the bar which shows Willy's relationship with his parents. It gets affected by the way certain situations are resolved, e.g. it increases if Willy refuses to play with his sister, and when it is full they send Willy to a military school and the game is lost.

The GOG release of this game for Windows includes both Floppy and CD versions of the game. The main differences are that the CD version has updated graphics, features animations and animated character portraits instead of static images, enhanced audio, and full voice-acting whereas the Floppy version doesn't feature any voice-acting.