April and May
Go nowAfter the winter crowd, before the summer one
The best window of the year: the rains are easing, the school holidays have not started, and prices sit between the two peaks. The whale season is tailing off in April and gone by late May, and the north shore is calming down enough to swim. Warm, dry, and the island at its least crowded.
September and October
Go nowThe warmest water and the quietest island
The other shoulder, and the one locals pick. Summer crowds have gone home, the ocean is at its warmest after a season of sun, and the north shore is still flat enough for snorkelling. Hurricane season runs through this period and rarely produces a direct hit, but it is the reason to keep travel insurance and a flexible plan.
January, February and March
Worth it, butWhales and giant surf, in the wet season
The wettest, cloudiest stretch of the year, and also the most spectacular. Humpback whales are in Hawaiian waters from roughly December to April, peaking in these months, and the north shore is running the biggest waves in the state. It is also winter escape season for North America, so hotels are full and expensive. Rain comes in bursts on the windward side and often misses Waikiki entirely.
November
Worth it, butThe wet season starting, the prices still low
The transition month: rain becomes more likely, the north shore swell begins to build, and the first whales arrive at the end of it. Prices are at their lowest right up until the holiday period begins, which makes early November one of the best value windows all year. Bring a plan for a grey afternoon.
June
Worth it, butDry and lovely, filling up fast
Weather is excellent and the summer south swell is starting, which makes Waikiki good for learning to surf. The catch is arithmetic: North American school holidays begin during the month and the island fills accordingly. Book early and it is close to a best window; book late and it is expensive.
July and August
Think twicePeak everything, at peak prices
The weather is genuinely good and that is not the problem. These are the busiest and most expensive months of the year, with families on school holidays, full flights, booked hotels, and queues at every trailhead and beach park. If your dates are fixed to these months, book far ahead and start every day early.
December
Think twiceThe wettest month meets the highest prices
The worst combination of the year: the heart of the wet season, and the holiday period that makes Hawaii one of the most expensive winter destinations in the United States. The whales arrive and the north shore surf is enormous, which is a real draw, but you are paying peak rates for the highest chance of rain. Come in November or come in April instead.