"Test the waters" with the help of locals
Experienced captains, especially local ones, are well familiar with specifics of a given region and are able to come up with 2-3 options for various weather and wind scenarios, as well as customer whims and preferences. However, if you are going to set out on an independent voyage, make sure you "test the waters" and find out what weather conditions to anticipate by, say, checking the weather for the same date range of recent years.