I used to work in Finance for Hawaii's biggest resort company and Hawaii is PACKED over Christmas break... Dec. 15 - Jan 7. << This is the worst time to visit (aka high prices, too many people). But.. the crazy thing is...hardly anyone goes on vacation the 2 weeks prior to the break. In fact, it is the least busy time of the entire year. So, plan a trip during the beginning of December, and that is when airline prices are the lowest, hotels drop their prices, the weather is awesome, the crowds are low, but the Christmas decor is up & the celebration is in full swing!