My wife and I recently went to the Hawaiin islands for a few days for a vacatoin. Here’s what worked well and didn’t well about the trip.


We stayed in resorts for the first time. This was new; normally we stay in Airbnbs or the like.


  • Consistent experience.
  • Clean and nice.
  • Pools and hottubs.
  • Safe. We felt very good leaving laptops and the like in the room.


  • Expensive. (Definitely not the most economical way to stay on the island.)
  • Close-by food and coffee quality was hit or miss on one of the two islands we went to. And it’s definitely was expensive in general.

Hawaii - The Big Island

We stayed on The Big Island and Maui while we were there.

The Big Island felt pretty rural and required a lot of driving to get to interesting places. It was also hard to find good food for a reasonable price. Neither of us love driving or being in a car for long periods of time, so while I’m glad I got to see it, we probably won’t be going back to this island because of this.

That said, there were some fantastic experiences we had while on The Big Island:

  • Swimming with Manta Rays at night. Highly, highly recommended!
  • Swimming with dolphins. Also highly recommended!
  • Viewing the active volcano from Hawaii Volcanoes National Park at night. This was super cool to see and was a nice night-time walk.

Hawaii - Maui

This island was awesome. We stayed in an excellent location and were close to good food, ice cream, and beaches.

We did significantly less driving on average because of how close everything was and this was exactly what we wanted. We also found several health-food stores (think: food co-ops) on Maui and visited them a lot; we didn’t find these on The Big Island (but in fairness, we didn’t look very hard so maybe they were there).

One awesome thing which happened is that my father-in-law got us upgraded to a two-bedroom suite at the resots. So we invited a friend a friend from Oregon to come join us last minute and she did! So we unexpectedly had a friend with us on our vacation, which was great.


I brought my Pelican 1040 Micro Case, thinking I’d put my phone in it. I didn’t end up using it for that all all. Instead, I used it to bring my contact case, eye solution, and other fragile items around with me. It was super useful. I really liked knowing that my fragile items couldn’t get crushed in my bags.

Day bag… I used my Goruck GR1 21L as a day bag. This worked super well, especically when I used the Goruck Shadow pockets to organize miscellaneous items (towels, spare clothes, etc.) I did find myself wishing I had my a small sling bag for outings where the backpack was overkill, though.

I used my two 4L GoRuck Shadow Pockets almost every day. It would have been nice to (a) have some different sizes (both larger and smaller) and be have different colored morale patches to identify them easier.

Apple Carplay

Both our rental vehicles had Apple Carplay in them. This was my first experience with it and it was absolutely awesome for navigation. I would go out of my way to get a rental car with Carplay in the future. (It also confirmed my desire to upgrade our car to a stereo with Carplay.)

Because we had to connect to the car with a USB A to Lighting cable, it basically used up my spare cable for the entire trip.

What to do differently next time

  • Bring both my Pelican cases with me; I wanted a smaller size several times.
  • Bring my Tom Bihn sling bag with me as well; only having my backpack for outings was silly when all I needed was to carry keys, sunglasses, and my wallet.
  • Buy some different sized and colored Shadow Pockets; it was sometimes hard to figure out what was what when they’re all black.
  • Bring at least one more charging cable than I think I’ll want; my one spare cable lived in our cars (for Carplay) the entire time we were there.