Designing sailing vessels for world-wide cargo transportation requires that the trade route and weather conditions are taken into consideration in the design process when design candidates are ranked. This work studies various strategies for representing the weather distribution related to the expected operational profile. The simplest approach is to decide on a single wind speed and direction as the design point. A slightly more complex method is to derive a statical distribution of expected weather and weigh the performance at each weather condition with its expected probability. The most demanding methods are route analysis using weather optimisation. The balance between accuracy and design work efficiency for the different methods is discussed and demonstrated for a wind powered car carrier concept. As an example, two design candidates are compared, and it is shown that the ranking differs considerably depending on which route representation strategy is used. To weigh the performance using the probability of the expected weather turns out to be an efficient method that gives similar results as the time demanding complete route optimisation. However, if the EEDI Global weather matrix defined by IMO is used for the weather probability distribution instead of statistics of the actual route, the ranking of the design candidates is rather different.