13 Top Highlights of Hawaii

Matt and Kelly begin their journey as digital nomads by spending three weeks amongst family and friends on the big island of Hawaii and Maui.

Green Sand Beach sunset with shaka in shot - aloha!

Now, Hawaii is a big (and expensive) place, so we focused on just two islands: Maui and the Big Island. We began our travels at Kona Airport; stepping off the plane and immediately realizing that we were overdressed (by about two layers) for the warm sunshine of the Big Island. However, after moment’s annoyance, we quickly let our tense impatience melt away as we realized we were really doing this year abroad – and we were starting in paradise!

Flight soaring through the hilltops of Maui, Hawaii. boldlygotravel.com

As we will no doubt address in other posts, we are traveling via a blend of hotels, hostels, and home-stays for our year of travel. However, we were blessed to find a real gem of a deal on a self-sufficient "ohana" built by the owners themselves on a lava field near Ocean View about an hour and a half drive out of Kona.

We knew that time was limited, so we decided to save relaxation for later in the trip as we dove right in to experiencing all that the southern part of the Big Island had to offer. In our five days on the Big Island, we sure did a lot:

#1 South Point (Ka Lae)

#7 Kona Coffee Plantations

Freshly picked coffee berries from Kona coffee plantations.
coffee beans from Kona set out to dry before being peeled and roasted
coffee farm dog at Hala Tree greets customers.
Couple enjoys Kona coffee tasting at Hala Tree in Kona, Hawaii.

#8 King’s Ponds

Some speculate that the bones of Kamehameha the Great were secretly buried in a cave nearby.

View of the Kings Ponds on Hawaii
couple has the whole plane to themselves as the fly to Maui, Hawaii. boldlygotravel.com

After dropping off our rental car at Kona Airport, it was time to head to Maui. We were in for a real treat as we were the only people on our 45 minute Mokuukukuku Air flight. Of course we paid more in baggage fees ($75 for our three bags) than we did for each person ($61), but we couldn’t complain about a private flying experience where we saw amazing views of the islands as well as a couple humpback whales breeching.

View of Maui from the plane. boldlygotravel.com
View of Molokini crater from a plane, Maui. boldlygotravel.com 

We spent a full 2 weeks in Maui because we had the good fortune of having excellent friends who lived in Kula (in the Maui upcountry where we ‘enjoyed’ an air mattress and shared bathrooms) as well as Kelly’s parents having a conference in Wailea (where they rented a 2 bedroom condo with a king bed and en suite bathroom). In different ways, we were glad to have had both experiences and share all out love and gratitude to those who helped make our long stay on Maui possible. While we definitely had to do more work during this part of our trip, we did manage quite a few adventures:

#10 Makena Bay and SCUBA Certification


#11 Road to Hana

Hawaii was everything we hope for as a start to our trip. With full bellies, happy hearts, and official SCUBA certification, we were ready for the marathon travel of the next two weeks before we get to Bali.

View from inside the Mill House Restaurant on Maui, Hawaii. boldlygotravel.com