There are three skill levels for each activity: Beginner, Intermediate, and Expert. In the game, the player engages in various sports events in Adventure World. JumpStart Around the World is essentially the preschool-2nd grade equivalent of Jumpstart Adventure Challenge. In the Advanced series releases, all eight activities are included.
Four more could be downloaded from the Internet during the game's initial release period. Originally, the game only had four activities. The third grade version was re-released with JumpStart Advanced 3rd Grade as Far Out Field Trips, the fourth grade version was re-released with JumpStart Advanced 4th Grade as Ultimate Field Trips, and the fifth grade version was re-released with JumpStart Advanced 5th & 6th Grade as Extreme Field Trips.
In 2003, JumpStart Adventure Challenge was re-released with the JumpStart Advanced series. It focuses on sports, and unusually for a JumpStart game, most of the activities have no educational value. It was included as a bonus disc in the Deluxe 2-CD set releases of JumpStart Adventures 3rd Grade: Mystery Mountain, JumpStart Adventures 4th Grade: Sapphire Falls, JumpStart Adventures 5th Grade: Jo Hammet, Kid Detective, and JumpStart Adventures 6th Grade: Mission EarthQuest. JumpStart Adventure Challenge is a game that was initially released in 2000.