Trip report introduction: Hawaiian island hopping!

Trip report introduction: Hawaiian island hopping!

01. Introduction: Hawaiian island hopping!
02. Alaska Airlines 737-800 economy class San Diego to Kona
03. Island Air ATR 72 Kona to Honolulu
04. Vive Hotel, Waikiki
05. Mokulele Airlines Cessna 208 Grand Caravan Honolulu to Ho’olehua
06. Mokulele Airlines Cessna 208 Grand Caravan Ho’olehua to Kahului
07. Mokulele Airlines Cessna 208 Grand Caravan Kahului to Kona
08. What to do when it rains for the entirety of your Hawaiian vacation
09. Grand Naniloa Hotel, Hilo
10. Hawaiian Airlines 717-200 economy class Hilo to Honolulu
11. Hawaiian Airlines A330-200 Extra Comfort (premium economy) Honolulu to San Diego

If you’ve never looked at how cheap inter-island flights are in Hawaii, do yourself a favor and hop on over to any Hawaiian airline website (,, or and poke around a bit. You can even do it right now – I don’t mind. I’ll be here when you get back.

It’s really amazing isn’t it? Apparently airline competition is fierce on the islands, because I really can’t understand how any of them can make money when nobody is charging more than $100 for a 1-way fare between pretty much any two points in the Hawaiian island chain.

Even more amazing is that I only paid $125 to fly from HNL to KOA on Mokulele Airlines for this trip, which included two stops on two islands along the way. How does that even begin to pay for fuel, landing fees, and staff expenses? I don’t know – and to be honest I feel worse the more I think about it. I’m really glad I’m not in the airline business.

So yeah. Island hopping! The itch to go to Hawaii again has been rather strong lately, and since I pretty much always just stick to Ohau, I felt like mixing things up a bit this time and doing something different. Using all my time to island-hop sounded fun, but I knew there was a pretty big downside to that: lack of time. If I chose to make this an island-hopping trip, there would be very little time left over for just sitting on the beach and doing my best impression of a Corona beer commercial. Do I or don’t I? That was the question I was batting around in my head for the days leading up to the reservation of this itinerary.

Obviously, I chose the island-hopping option. It’s something I’ve always wanted to do, and it’s not like I’m never going to Hawaii again, so why not?

Piecing together the itinerary

I’d like to dedicate a few words to the booking process for this trip since it ended up being more difficult than usual. First of all, I had to find flights to and from Hawaii that weren’t outrageously expensive. Hawaiian and Alaska fight pretty hard for Hawaii-bound passengers here in San Diego, so it wasn’t too difficult to find a weekend with reasonable ticket prices.

With that out of the way, it was a matter of trying to find a way to try every single one of the big Hawaiian airlines. There are only a handful, but it did take me an entire day to piece together a complex itinerary that would get me on all of them except for ‘Ohana. No biggie – I can always try them later I suppose.

So there I was, sitting at my desk with my notes in front of me, the itinerary all planned out and ready to start booking reservations. There were many segments with very specific times to purchase, so I made a mental note to concentrate and take my time during the booking process so that I wouldn’t screw anything up.

Apparently I wasn’t concentrating hard enough, because I botched the very first purchase. Yep – I mistakenly bought a ticket on Island Air (KOA-HNL) for Sunday instead of Saturday, which just wasn’t going to work. Ugh! Not a good way to start, but thankfully this was only a $75 ticket so it didn’t hurt too badly to purchase another one for the correct day. Way to go Scott!

That little error forced me to concentrate even harder, and I was able to obtain the rest of my itinerary without incident.

Here are all the flights I purchased:

04/29/17 AS185 economy class San Diego to Kona (737-800)
04/29/17 WP85 economy class Kona to Honolulu (ATR 72)
04/30/17 MW600 Honolulu to Ho’olehua (Cessna 208 Grand Caravan)
04/30/17 MW600 Ho’olehua to Kahului (Cessna 208 Grand Caravan)
04/30/17 MW728 Kahului to Kona (Cessna 208 Grand Caravan)
05/01/17 HA371 economy class Hilo to Honolulu (717-200)
05/01/17 HA16 Extra Comfort (premium economy) Honolulu to San Diego (A330-200)

Sounds like fun, doesn’t it? I thought so. Even though I wouldn’t have very much beach time for this trip, I was still looking forward to it in a pretty big way. Two new airlines, three new airports, a new Island – I was very excited about all these new-to-me experiences!

hawaii island hopping itinerary
Here’s a close up map of Hawaii showing all the segments of this itinerary.

That being said, now that the trip is over and I’m back at home writing this trip report, I don’t think I’ll ever do an island hopping trip like this ever again. It was fun, but apparently I’m much more prone to motion sickness than I thought and…well…

I’ll save that story for the trip report. 😃

Comments (3)

  1. John S

    May 25, 2017
    • SANspotter

      May 26, 2017
      • John S

        May 26, 2017

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