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Save this Post. 2. Re: September weather in Maui & how many days. Dec 11, 2009, 12:50 PM. Weather in Sept. is generally very warm. Upper 80's. Not part of the rainy season, unless of course, there is a hurricane lurking around somewhere. I recommend at least 10 days.
The best times to visit Maui are April through May and September through November. The spring and fall shoulder seasons provide the pleasant weather Hawaii vacationers seek without the high rates and heavy crowds that accompany the summer and winter. However, if you're into surfing, you'll want to travel in the winter for the best conditions â just book as early as possible to get a discounted rate.