Kaanapali in January

April through June offers the sweet spot of great weather, fewer crowds, and reasonable hotel rates. September through November delivers similar conditions with the bonus of humpback whale season starting in late fall. December through March brings peak crowds and prices, but also the best whale watching and most consistent surf. Summer months can be hot and humid with occasional trade wind interruptions. Here's what most guides won't tell you: shoulder seasons mean some restaurants and activities might have reduced hours, but the trade-off in crowd levels makes it worthwhile. Avoid the weeks around Christmas and New Year unless you book months ahead and don't mind paying premium prices for everything.