The first questions people ask me about traveling to Hawaii are When should I go? and When is the BEST time to go to the islands?
My stock answer to these questions is ALWAYS!!
But that may not be entirely true. If you are looking for specific attributes–weather, snorkeling, big surf, whale watching, deals–you have to know the moods of the islands. So choosing when to go, and of course which island best suits you, is a major consideration.
Deals: If you are looking for deals to Hawaii, you can forget celebrating Christmas in the state, when hoteliers jack up prices to over three times what they are in the shoulder season. Summer is considered value season for accommodations, but airlines see school breaks as time to charge a ridiculous amount to go anywhere.
So for the best deals to Hawaii, you have to go in October and early November, the first week of December, and again from late March to early May.
Weather: I know, this sounds like a joke, right? Weather in Hawaii is usually pretty darn perfect. However winter can be rainier and you will need a sweater after dark. And summer can be downright hot on some parts of islands. That being said, summers can be just as wet, so always prepare for rain, and learn to love that precipitation.
Whale Watching: Wintertime brings hordes of whales to the archipelago. And what a show they put on! December-March is a great time to get up close and personal with these massive creatures.
Boating & snorkeling: In general, adventure outfitters go out year round. But trips do get cancelled due to overly choppy conditions on the seas. For your safest (and least barfy) chance to see the Na Pali Coast, head out in summer.
Surf: Big wave surfers descend on Hawaii’s north shores to ride the massive wintertime surf. For those less experienced, the waves tend to be gentler in summer.
As I said, anytime is a good time to trek to Hawaii. For detailed itineraries, pick up a copy of Backroads and Byways of Hawaii.