Hawaii Travel Tips 2020 Fall and Winter

Hawaii Collage by Heidi Siefkas

As a resident of Hawaii and travel lover, I wanted to share a little aloha with my simple Hawaii travel tips for Fall and Winter 2020. For many months now, Hawaii's travel rules and regulations have been changing by the day faster than the weather atop Haleakala. Instead of surfing the web and wasting previous travel planning time, I wanted to clarify how you can travel to Hawaii after October 15th, 2020, and give you some basic Hawaii travel tips for 2020. Below I will outline the rules and link to trusted Aloha State sources.

How can you travel to Hawaii in 2020?


Two-Step Process:

Step 1:

As of October 15th, 2020, trans-Pacific travelers with a negative Covid-19 with 72-hours of the final leg of travel, may bypass the mandatory two-week quarantine. That means those from the continental U.S. can now fly to Hawaii. However, not just any Covid-19 test will do. There is only a selected list of trusted testing partners, many of which have aligned with airlines flying to the Hawaiian Islands. You can view the testing partners and more detailed Hawaii travel info here.

Step 2:

Once you have tested negative and are within 24-hours of flying, you must register with the State of Hawaii. Last month, I did not know about this requirement prior to arrival. I needed to fill out on my Smartphone in the terminal before claiming my bags. My advice is to do it at home where you have a good internet connection. This will make it easier and faster upon arrival.

*Be aware, Big Island, Hawaii requires a second test upon arrival; whereas, Maui and Kauai ask visitors to voluntarily take a second test at the counties' cost two-four days after arrival. So far, Oahu has no second test regulation as of yet.*

Where to stay in Hawaii?

It depends on your travel style; however, I do have two favorite types of accommodations that can keep you and your travel companions safe: your own vacation rental with Turnkey or off-the-beaten-path camping/cabins with HipCamp.

What to do in Hawaii?


This is a loaded question with multiple answers depending on your interests, time of year, and of course which island you are visiting. Currently, I live on Maui which has a bit of everything; thus, the Valley Isle has something for everybody. However, I have also lived on Kauai and visited all the major Hawaiian Islands. My number one tip for discovering things to do in Hawaii is to use Viator to locate a local tour operator that can customize your activities. Maui activities range from snorkeling Molokini crater to whale watching and Haleakala sunrise to horseback riding. Kauai adventures also range from kayaking Wailua River, a helicopter tour of the Garden Island, snorkeling in Poipu, or kayaking Wailua River. Big Island's fun things are swimming with the glow-in-the-dark manta rays, visiting Volcanoes National Park via helicopter, and chasing waterfalls near Hilo. On Oahu, there are many tours and options to do hiking Diamondhead, visiting Pearl Harbor, kayaking the Mokes, and diving with sharks.


What if you live on one of the Hawaiian Islands and want to visit a neighbor island (interisland travel)?


There have been many changes opening and closing interisland travel in the Hawaiian Islands since the beginning of Covid-19 in March 2020. The most recent change with interisland travel is like the pre-test for visitors coming from the continental United States. All Hawaii residents will need to test negative 72-hours prior to visiting Maui and Kauai.  In fact, Oahu has no pre-testing mandate from neighboring islands. You can view each Hawaiian island’s travel regulations here.

Hawaii Travel Tips for 2020


*Pack sunscreen, sunglasses, swimsuits, hat, slippahs (flip flops), mask(s) (N95 and snorkel mask), and hand sanitizer.

*Arrange for your approved Covid-19 test 72-hours before flying.

*Register with the State of Hawaii 24-hours prior to flight.

*Purchase travel insurance for any travel or health hiccups.

*Rent a car – Popular choices are 4WD, convertibles, or compacts for easy parking.

*Start reserving your adventures and pay later

*Live Aloha: respect the aina (land), residents, and other travelers by maintaining social distancing and wearing masks when unable to social distance.

If you have questions and/or comments about Hawaii travel in 2020, please leave below.

I look forward to sharing many more Hawaiian adventure stories with you.

As always, here’s to looking up wherever you are.


2 Responses

  1. Looks like you have the system all figured out. I'm still trying to find out what happens if I just need to go to Oahu for the day. We are holding our Zonta Club of Kauai meetings via Zoom. If you ever get to Kauai, let me know, so you can attend as my guest. Aloha!
  2. Heidi, are you actually living in Maui? I was on a trip with you to Cuba a few years ago. We Have been traveling to Maui and Oahu for 40 years. We had to leave early this year because of COVID, but are booked to go back this March, hopefully. If we get there I would love to catch up with you. Stay safe.

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