Wailea in January

April through May and September through November hit the sweet spot – warm weather without the crowds or peak pricing. December through March brings humpback whales offshore, but also the highest hotel rates and packed beaches. Summer (June-August) gets hot and humid, plus it's peak family season. The shoulder months give you the best weather for golf and fewer people fighting for pool chairs. Trade winds keep things comfortable most of the year, but they can get gusty in the afternoons. Rain is rare in Wailea – this is the dry side of Maui – but when it comes, it's usually brief afternoon showers. Hurricane season runs June through November, but direct hits are uncommon. Book at least 6 months ahead for winter visits, 3-4 months for other seasons.