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Hawaii Late Summer/Fall: Hawaii Deals++!

One of the questions we are asked most frequently is when to plan a Hawaii vacation. Obviously everyone’s needs are different, but having said that, here’s our unequivocal answer. With the end of summer already in sight, autumn in Hawaii – our favorite season, will soon be upon us. With it comes Hawaii deals, no crowds, exceptional weather and days that are slightly cooler and shorter. As the sun more angled, the light makes everything in Hawaii even more beautiful.

1. Hawaii Travel Deals valid for Late Summer and Fall from $199

For as little as $199 one way, including tax, you can fly Hawaiian Airlines this summer and fall between west coast cities and the Hawaiian Islands. This isn’t just for the west coast either. There are flights from Phoenix, Minneapolis, Boston and New York – all at great prices starting August 8.

2.Fewest Visitors in Hawaii

The peak summer travel season officially ends August 7. From then on you will find  the best deals of the year for airfare, accommodations, and activities. There will be fewer visitors in the islands. You can have beaches all to yourself, find less traffic, plan spontaneous activities and walk up to favorite restaurants without reservations. In a word, it’s idyllic.

3. Hawaii Weather in Late Summer and Fall

Annual Hawaii rain usually occurs twice. The first is sometime in November or December (the other is March or April). So you have plenty of time to visit before then and even select areas to stay or play that are typically wetter at other times of year. That’s more great news for those planning a Hawaii vacation this fall.

Other than occasional tropical storms, the rain pattern is mostly away from the beach, in what is called “mauka” or mountain based showers. These are generally brief and occur at any time, though often at night.

The mauka showers are an aspect of our prevailing trade winds (Hawaii’s air conditioning), and cross the islands from the northeast to the south west, leaving the south and west sides generally warmer and dryer.

So while our mountains and valleys receive rain, it generally remains dry at the coast. This is typical of Hawaii’s micro climates.

21 thoughts on “Hawaii Late Summer/Fall: Hawaii Deals++!”

  1. We will be traveling to Kona in October from Tampa, Florida. I have read that prices should go down some beginning around August, but I am also afraid that if I wait too long to buy tickets that they’ll just keep going up. Also, we’re going to Honolulu after the Big Island. So I was thinking the best route would be Tampa-Kona-Honolulu-Tampa or would it be better to do Tampa-Honolulu round trip, then buy inter-island airfare from Honolulu-Kona? Mahalo!

    1. Hi Lissa,

      There’s no market between Tampa and Hawaii, so we only expect seasonal fluctuations rather than sales. There’s an $842 fare on United with a speedy 1-stop connection using your routing (fine to do it either way you mentioned). Plus the cost of inter-island (oh and buy that sooner than later for best options on time of day and seats). There are cheaper fares on Alaska but they take twice as long or longer.


  2. We are looking to travel to Hawaii the first two weeks of November, heading to the Big Island and Maui, maybe a couple of days in Kaui. Starting to plan our trip, but the airfare for us is tough as we start out in a smaller airport and will have to make at least two connections on either end. We are leaving out of GSP and the best options for us will be Delta with connections in ATL or LAX, or American with connections in DFW or PHX. I’m a little worried about doing a long flight from ATL or DFW straight to Hawaii and am wondering your thoughts. Any other options/airlines we should look at?

  3. My senior mother and
    I would like to travel to Kauai, from Oakland/or SF maybe Sept or October, when all the kids are gone, and it’s quite… whats your recommendations as far as a place to stay homey, with kitchen, etc by the beach?

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