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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 peak season for whale watching on Maui is January, February, and March, though whale season in Maui officially runs from December 15-May 15. Early in the season, the first sightings are usually of males who have made the swim from Alaska, awaiting the females who usually show up between Thanksgiving and Christmas.