The paper is about characteristics analysis of major winds across the Croatian part of the Adriatic Sea and their impact on organization of sailing ship navigation from prehistory until mid nineteenth century. Research area was divided into northern, middle and southern part of eastern Adriatic, and parameters for three prevailing winds – bora, jugo and mistral, were observed over four climatological seasons and also over annual average values on 18 main meteorological and climatological weather monitoring stations. Information generated from such data was intertwined with archaeological findings from the eastern Adriatic coast and historical writings that witness sailing across the area. Historical writings that were used consist of itineraries and some of the earliest nautical pilots written as a navigational aid for the area of the eastern Adriatic. The prime goal was to determine if there is a correlation between reconstructed sailing routes that existed in times when information about landscape and surrounding occurrences and processes (wind in this case) was collected by observation and contemporary measured data. It was also important to determine if navigation was affected by advances in nautical technology, particularly ship hull and sail construction, and navigation equipment.