Wailea in September
Great time to visit
Summer heat lingers but crowds thin out after Labor Day. One of the better value months if you can handle warm temperatures and don't mind potential weather monitoring.
Weather
September weather starts cooling slightly as trade winds return more consistently. Humidity begins dropping, making warm days more comfortable. Rain patterns become less predictable but still brief when they occur.
32°C high24°C low4 rain days
Crowds & Cost
moderate crowds
~$360/day average
Events & Festivals
- •Aloha Festivals begin
- •Labor Day weekend surge
September Tips
- •Post-Labor Day rates drop significantly
- •Hurricane season peaks - monitor weather reports
- •Perfect time for sunset dinner cruises with calmer seas
All Months
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.
Wailea Scores
Solo
6/10
Couples
9/10
Families
7/10
Adventure
4/10
Budget
2/10
Luxury
10/10
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