Formula Kite is a high-speed sailing sport using hydrofoils, recently included in the Olympic sports list. In Formula Kite, the riders’ technical abilities to reach and maintain high speed are key to achieving performance. The aim of the present study was to analyze Formula Kite riders’ performance during speed tests in practice sessions by combining qualitative descriptions of their lived perceptual experiences “from the inside” with measured correlates of performance. The courses of experience of four expert Formula Kite riders’ speed tests were analyzed, compared, and discussed in relation to their measured Velocity Made Good. Results of the qualitative analyses provide original insight into the fine technical adaptations of the riders in their pursuit of performance. Furthermore, the comparison between the evaluated performance using speed measurements and the perceived performance assessed by the qualitative analysis shows interindividual differences as well as inconsistencies between the two modes of analysis. Based on these results, the present study opens practical perspectives for improving training practices, consisting in “calibrating” the sailors’ perceived performance with measured performance.