The American Challenge: A Sailing Simulation is a sailing simulation which features eight courses. The player races against computer opponents and has to steer the boat and sail the trim and centerboard position. During the race all boats are shown in wireframe 3D graphics and the player can always switch to an overhead map which shows the contestant's path up to this point.

If the player doesn't want to sail against the computer anymore, he can trade the sail boat with a high-speed motorboat or start a multiplayer match.

The game can be played with up to 2 players, however, 2 player mode requires a modem. One of the earliest examples of online play