I look at several factors when deciding when to take a trip to the islands. Weather, cost, and busy travel times tend to be the most important factors I look at.
The beauty of Hawaii is that you have great weather year round. We will tend to get a little more rain though between November and March. Now being born and raised in California, that little bit of rain never bothered me. Temps will still be warm. The rain typically is short and sporadic. Meaning it's still beach weather for me as well as most my friends that have transplanted to the island. Keep in mind though, the days will be shorter around these months as well, sun usually going down around 5:30-6pm. In short, Hawaii is a great destination year round.
When choosing my dates of travel, I tend to avoid June through early September, month of December, near major holidays, and around spring break. These are typically the busy seasons which constitute higher airfare and often higher hotel rates.
Other than the aforementioned times, I will usually Google a calendar of events on Oahu, to see if there are any big events during the times I am considering. For example, going during the Vans Triple Crown (surf contest) means that travelling to or through the North Shore can be very long and difficult. If I travel during the Honolulu Marathon, hotels will be expensive and there will be much traffic in parts of the island. I'm not saying you can't go during these times. For some these would be great events to experience. I simply do not enjoy the traffic and crowds at times.
There is no bad time to go to Hawaii, though some times may be a little nicer for some travelers.
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