Sailing charters on Maui are generally not ‘stand alone’ sailing adventures. Usually they will be a snorkel, sunset cruise or other trip that will include sailing as a part of the tour. There are some rare tours that are designed to get you out into the stiff afternoon trade winds but these are few and far between. It is much more likely that if you are on a sailboat, for example, that is traveling over to Lanai for the day, that they will put the sails up on the return voyage to take advantage of the experience of a sail.
Many more sailboats will make use of the gentler ‘temperature differential’ breezes that will naturally come up in the late afternoon hours. Quite often these boats will go out under full sail but the speeds attained would be no where close to those speeds that could be attained during a mid-afternoon sail. In all honesty, the lesser wind velocity of in the late afternoon fits more in line with the ‘gentle breeze’ ambiance that works best on a romantic sunset sail.