In Sailing, the player participates in a sailing league with the goal to reach the top. Each event has the same basic procedure: the player challenges another boat, up to two places above in the league ranking, to a race and based on the opponent's ship and the weather report, there are various changes to the own ship to be made, e.g. the overall length or the hull material. Before beginning a new league, the player chooses a skill level which determines the starting place in the ranking and therefore the difficulty level of the next opponents.
The races itself take place from a first-person perspective and involve following a course while being faster than the other ship. The information gained from the display on the bottom of the screen - wind strength, wind direction, boat speed and a mini map - should be used to find out the best course of action. The player can rise and turn the spinnaker, but then no manual steering is possible.