Hawaii in October?
#3
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It is not accurate to say that Wailea is the only part of Maui that does not have "iffy" weather. Kihei has the same weather, and in fact the weather is very good all the way up the west side to Kaanapali. Any farther north on the west side and it MIGHT be wetter, especially in winter. Also, because Wailea is so dry it is also not as lush and scenic as some other parts of the island .
#8
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My wife and I spent the first two weeks of October last year visiting the Big Island, Kauai and Maui. The weather was fine everywhere... one rainy day on Kauai but it didn't matter to us. The surf was up however so snorkeling on Kauai's north shore was occasionally tough.