When is the best time to visit Hawaii? It depends on three things.
(1) the best weather in Hawaii
The first time I visited Hawaii was for a conference, so I had no control over the timing (and was not paying the bill). When I wanted to return, I wondered about the best time to visit. My previous experience with a tropical environment was south Texas, with severe winter rains and an April 1 temperature of 100 degrees. I had no idea Hawaii weather was so uniformly balmy. However, local residents notice cooler temperatures in the winter and warmer ones in the summer. If you have complete control over your schedule, a spring or fall visit is most likely to produce stellar weather.
(2) the price for airfare and hotels
In addition to the weather, the second concern I had was with the cost of travel. Unlike Colorado’s ski resorts, for example, the rates in Hawaii are not pegged to conditions here. The busiest times for travel, and the most expensive, are when school is not in session. Avoid spring break, summer and winter holidays for the best prices. Oddly, that has you paying more for visiting when the weather conditions here are not as good. The key is that they are so much better than the mainland at any time — cooler in summer and warmer in winter.
(3) the weather where you are
My brother called last fall to say he wanted to visit Hawaii for Christmas. I explained that it is one of the most expensive times to travel here, that both the weather and the rates are better in the spring or fall. “But sis,” he replied, “I’ve just got to get out of this snow!” The value of being in Hawaii rather than Colorado is much higher for him in the winter (Colorado has wonderful summers). Often, the best time to visit Hawaii depends more on where you’re coming from than the conditions here. So, this is for people like my brother: book now for Christmas. It will still cost more than traveling in October but getting an early start helps.