First off, the time of day you take your flight can be more important than any overall weather pattern. As a general rule, as far as Maui helicopter flights go, the earlier in the morning you take them the more likely it is that you will have great weather. The trade winds blow on the island about 300 days a year and they come from the north-east and usually don’t impact the island until mid-to-late morning or early afternoon. The most pristine, clear and wind-free conditions are generally in the early morning starting with the 8am flight and progressing to 9am, 10am and so forth. This of course does not mean that all afternoon flights will not be as good but simply that the odds are in your favor by leaving earlier in the day.
Secondly, the time of year you choose to go can have an impact on the weather you will be experiencing on your helicopter flight. Once again, following generalities, the best weather conditions for a flight will be when we have trade winds which are more likely to blow in the spring, summer and fall. Strong “Kona Winds” are most often reported in the winter months and these are the winds that will also likely bring rain. So this leads to the question, if it’s raining is it a bad time to go up on a helicopter flight? The answer is quite honestly yes or no. Keep in mind that Maui is an island and is being buffeted by winds and likely rain somewhere on any given day of the year. Just because it may be raining where you might be does not necessarily mean that it is raining everywhere.
The best rule of thumb is simply to trust the helicopter company for advice. Certainly they want very much to take you up for a flight but they have a vested interest in showing you a good time. The last thing they want is to take you up on an unsatisfactory flight that you may have a negative reaction to. No one wants to deal with a cranky client who feels he or she has spent their money unwisely. In most cases helicopter companies know from previous flights what the weather conditions around the island are and they are apt to cancel an upcoming flight if the previous ones were not stellar. On many occasions the rainy conditions will only be on certain parts of the island and these areas can be circumvented by altering the course of the flight somewhat. On such days it is almost always still worth it to go up for a tour as opposed to not going at all.
During periods of bad weather scheduling your helicopter can be quite difficult. When a couple days are cancelled because of poor conditions they are often followed by excellent conditions and there may often be a rush to find flights during those good times. Remember that, just like everything else, weather occurs in cycles and bad weather will always eventually turn into good. The wisest thing to do in most cases if you are cancelled for bad weather and if you are on the island for a few days is to be proactive and make a booking in the morning hours for a day three days out. This way you will avoid the rush of people who are simply waiting for the weather to change before they make a booking and are often responsible for causing a log-jam in flights. Remember that if it is still raining three days hence you haven’t really lost anything but you will at least have a guaranteed flight time if the weather turns good.