Direct answer
Objectives follow journal display order. Some depend on your choices; follow the active objective in the game.
Result
Kaer Trolde was host to something called the Helmsman's Dash, a race in which the best sailors from all of Ard Skellig took part. Geralt decided to prove to the islanders that a Continental man such as himself could guide a boat as well as any islander and so entered the races.