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.
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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!
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.
Aloha.
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?
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?
I’ve been working on a trip to Hawaii for months. I’m THINKING that I’ll fly into Oahu a few days, then to Kauai (I really want to do the plantation tubing) & then spend a week or so on The Big Island. I’ve been to Hawaii several times & have family in Kona & Oahu. I’m looking for my own accommodations but my Niece said inter island flights are exspensive. Are they? Also, I have a Hawaiian Airlines CC & plan to use my points. Would it be best to pay them (it’s an extra expense) to handle my travel or should I do it myself?
Hi and thank you for providing such a helpful site! We are planning a 50th anniversary trip to Honolulu, Princeville, Kauai and Kahana, Maui Oct. 26 – Nov. 19 from Boston. Any flight advice would be much appreciated!
Thanks so much,
Pat
Hi Pat.
You asked that question yesterday at we answered it as 12:04pm. Do you see that reply?
Aloha.
Hi Again, I’m sorry and I feel like a nuisance but I can’t find your reply. I can’t imagine how I could have missed it because I have been watching for it but obviously I did. Can you help? And thank you again!
Pat
Hi Pat.
No problem. Here it is below.
Aloha.
“Sounds like a great trip. Only bad news is the airfare. That’s going to be $1K on American with a fast connection from Boston. Outbound in October might have lower fare later. You can try waiting but the return might be a problem in terms of availability as that is the Friday before Thanksgiving week, and is best booked sooner than later. Therefore, no great suggestions. Just as a note, there’s a $600 RT from Boston to Maui late/summer to fall, which won’t help you in terms of dates or flying into HNL. But it gives an indication of where prices can go off-season from Boston.”
Hi- thank you for your helpful tips to plan our trip to Hawaii. My daughter has been living in Oahu for the last 6 months and my husband and I are planning our 1st trip to the islands for early September. We would like suggestions on:
1. best rates and time to book airlines from the Washington DC area, preferably Dulles (IAD) airport to Honolulu
2. We plan to visit with daughter on Oahu and then the 3 of us fly to the islands of Kauai, Maui, and the Big Island so we are looking for:
A. best priced flights to and from these islands and can we get a packaged deal on interisland flights?
B. Information on most affordable accomodations for 3 adults for 5-7 days stay on each of the islands, (we would prefer to rent an efficiency or one Bedroom apartmentfor 3 adults, so we can make our own meals and drive a rental car to see the sites).
Thank you for your prompt reply.
Hi Judi.
Cheapest times to fly are found here. Cheapest prices for fall are starting at $769 to Honolulu. There are packages flying inter-island although we’re not convinced they will save you money. For accommodations we’d suggest starting by having a look at the Hawaii Revealed series of acclaimed online and print guidebooks.
Aloha.
Is there usually a big difference in price for September? Do you know if Delta gives any refunds on the difference in ticket price per person?
Great site and lots of excellent info!!
😆
I am looking to go to Oahu over Thanksgiving. When should I to book my airfare and hotel to get the best deals.
Hi,
Is $498 rt from sea to maui for end of sept a good deal? Should I wait till it gets lower to $430 like a few months ago? When do you think there’ll be another sale?
Thankyou
Hi Laline,
It seems like there’s at least $50 that could be saved by waiting. No harm unless you are traveling on Saturday which might not improve.
Aloha.
My husband and I have waited 25 years to take a vacation to Hawaii!
Is February/ March a good time to go? I’m so excited! I can’t wait!!
Hi Juli.
There’s never a bad time to visit Hawaii, which is one aspect of what makes it unique. It is definitely cooler and rainier then then but still a great time. Daytime temperatures perhaps high 70’s to 80 – depending on where you are staying.
Aloha.
Stay away from mid to late March Spring Break & Easter are a killer!! End of Feb first week in March were good, lots of whales!! We were on Maui 3/23/16 to 3/30/16 never again at that time.
Is mid November considered to be fall or winter? Does it tend to rain in Kauai or Maui around this time?
I also find the snorkeling to be the best in the Fall!!