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Authors in this paper presented the analysis regarding influence of deck equipment positioning and trimming, which is directly connected with sails, on sailing yacht performance in sailing. The analysis is performed by on-field measuring during sailing using specialized equipment based on RaceQs application and GPS support. The analysis is related to light wind conditions without significant waves, then to moderate wind and waves and finally to storm wind and high waves. Data collecting was performed during 30 hours of measuring and monitoring where the relevant equipment was continuously repositioned and trimmed aiming to reach more boat speed for different sailing angles. The results are processed and presented. The research was enabled with help and support of Bavaria Yachts d.o.o. Further analysis is suggested for different wind conditions and sea states.