In search of key-performance predictors in sailing, we examined to what degree visual search, movement behaviour and boat control contribute to skilled performance while rounding the windward mark. To this end, we analysed 62 windward mark roundings sailed without opponents and 40 windward mark roundings sailed with opponents while competing in small regattas. Across conditions, results revealed that better performances were related to gazing more to the tangent point during the actual rounding. More specifically, in the condition without opponents, skilled performance was associated with gazing more outside the dinghy during the actual rounding, while in the condition with opponents, superior performance was related to gazing less outside the dinghy. With respect to movement behaviour, superior performance was associated with the release of the trimming lines close to rounding the mark. In addition, better performances were related to approaching the mark with little heel, yet heeling the boat more to the windward side when being close to the mark. Potential implications for practice are suggested for each phase of the windward mark rounding.