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If you’re a long-time reader of the site, then you know that I am a sucker for crazy roadtrips and other geographical oddities. Part of this is from my longstanding goal to visit every county in the United States (I’m about 70% of the way there) and just a general interest in seeing interesting sights. Recently, while my family and I were in Hawaii, my son and I took one day to visit every county in Hawaii. There are only 5 counties in Hawaii, but it includes Kalawao County, which is literally the most difficult county to visit in the entire United States.

(SEE ALSO: How far would you go to meet a travel goal?)

Previous County and Strange Geography Trips

This isn’t the first time I’ve done something crazy like this. Here are links to a few previous county trips with similar endeavors

As you can see, while to you it might seem a bit strange to take 5 flights in one day, it is certainly not out of character for me 🙂

5 Hawaiian Inter-Island Flights Itinerary

Here was my scheduled itinerary

  • Kahului (OGG) – Kona (KOA) 7:10 7:59
  • Kona (KOA) – Lihue (LIH) 8:40 9:36
  • Lihue (LIH) – Honolulu (HNL) 12:30 13:10
  • Honolulu (HNL) – Molokai (MKK), with a stop in Kalaupapa (LUP) 14:30 15:34
  • Molokai (MKK) – Kahului (OGG) 19:30 20:00

The first, fourth and fifth flights were operated by Mokulele Airlines in a Cessna, while the 2nd and 3rd flights were operated by Hawaiian Airlines on a Boeing jet. The total cost for the 5 flights was about $300 per person.

Astute county counters will know that starting your trip from Maui (Kahului) is suboptimal, since you are pretty much required to visit the island of Molokai on your trip, and Molokai is also a part of Maui County. But since we were already spending the week on Maui, that is where we needed to start our trip.

Flying 5 Hawaiian Inter-Island Flights In One Day – the first flight goes wrong

We started off bright and early, with my wife driving my son and I over to Kahului Airport (about 30 minutes from our Vacasa vacation rental) bright and early. She dropped us off at the main terminal, but I could not find Mokulele Airlines anywhere. Eventually I asked an employee and she told me that Mokulele operates out of the commuter terminal (in hindsight, it makes sense). I called my wife and thankfully she had not left the airport yet, so she picked us back up and after a bit of stumbling around in the dark, we found the right place. Since there are less than 10 people on the airplane, there is no TSA or security. Instead, we checked in and then waited in the only room / area that there was.

There were a lot of people there from earlier flights that hadn’t left yet, and I started to get a bit worried. It was this first connection of the day that was our only really tight connection, and it didn’t help that we were flying two different airlines.

(SEE ALSO: Connecting flights on different airlines: When it’s a bad idea)

Eventually, we took off (a bit late) but I was right to be worried. We landed at Kona at 8:27, for a connecting flight that was supposed to depart at 8:45, from a terminal half a mile away. On the positive side, I did get to hear my name over the airport intercom for the first time ever!

(SEE ALSO: Miller… Party of 2… Please Make Your Way to Gate 9…)

(SEE ALSO: I have 2 rules of traveling (for when things go wrong))

5 Inter-Island Flights In One Day – 2 flights on the same plane

Thankfully we made it and were off on our 2nd flight of the day, to Lihue (Kauai County). We were supposed to have about a 3 hour layover, but when we arrived in Lihue, I realized that the plane we just landed on was going to Honolulu. So I asked the gate agent if we could move ourselves up to this flight instead. That wasn’t a problem, and instead we got to have a longer layover in Honolulu, where we at least could access the HNL Plumeria Lounge via Priority Pass.

Flights 4 and 5 – finishing up our Hawaiian Adventure

After a bit of time in the Plumeria lounge, we considered visiting the other HNL Priority Pass lounge, but I’m glad we didn’t, since it turned out that was literally the worst Priority Pass lounge in the United States. Instead, we took the “wiki wiki” intra-terminal bus over to Terminal 3, which is where Mokulele Airlines flies from.

We got there quite a bit early, so we had some time to kill while we waited for our flight to Kalaupapa (Kalawao County) and Molokai (part of Maui County, though we had already been there at the start of our day).

After we finished our adventures on Molokai and visiting Kalaupapa, we took our taxi back to the Molokai airport.

(SEE ALSO: Kalawao County Hawaii Trip Report (the hardest county in the US to visit))

We were originally scheduled to take a 7:30 p.m. flight back to Kahului (Maui), but were once again able to get on an earlier flight. There were some delays with the flights, so our 4:30 flight didn’t end up taking off until nearly 6pm, but it still meant that we got back home a few hours earlier than we thought we would. It was a fun day, but a tiring one, and it was nice to be back home.

The Bottom Line

Yes, I understand this may not be the way that you (or most people) prefer to travel, but it made for quite the adventure, and of course, got me 5 counties closer to my goal of all 3,143 counties in the United States. Other than a stressful first connection (including an unexpected half-mile run!), the rest of the day went pretty much according to plan.

Do you have any fun roadtrip stories like this? Leave them in the comments!

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