We are thinking of booking a trip for 2 weeks after Christmas this year to Maui. I am a little concerned with the weather. Has anyone been there over the winter break?
Is it the rainy season? Is everything packed during this time of the year? I'd appreciate all feedback.
Thanks

It is the rainy/cooler/cooler water season. It's mostly good weather, but there could always be days to ruin a beach day. Best weather is in the Wailea area, not Kaanapali/Kapalua at that time of year.

P.S. Nearly guaranteed good tropical weather in winter is in the Caribbean, where it is the dry season and the water temps are like Hawaii in summer (80+)

Was in Maui over the Christmas holidays this past year. I was more concerned about how crowded it would be moreso than about the weather. We stayed at the Hyatt which was at full capacity. I really wouldn't have known that it was any busier than any place else that I have been at any time of year. The weather was AWESOME and we had a great time.

The weather couldn't be much rainier on the islands than it was this past month...LOL! Wailea will be a good bet for dry sunny weather. It's a busy time for Hawaii but that wouldn't deter me. It's not going to feel crowded or packed there regardless IMHO.

Thanks for all your comments. I guess the crowds really don't deter me either with the exception of being able to book something that isn't extremely overpriced due to demand. I planned on staying in Wailea and Kaanapali. Maybe I should rethink Kannapali---we stayed there several years ago in February and it did get chilly with the trade winds. Hmmmmmm....

If I were to add another island (strickly for a chance of better weather) What do you think? I've been to Kauai, Hawaii, and only 3 days in Oahu. What about Lanai? Which areas to stay and avoid for weather?

Lahaina and Kaanapali is in a dry area of Maui.

Just north of Kaanapali in Kapalua, it does rain more.

South Maui (Kihei, Wailea) is also fairly dry.

East Maui, especially on the Hana side gets a lot of rain.

The resort/hotel areas on all of the islands are generally in drier areas.