TL;DR

• Stay
  • The Westin Los Angeles Airport, 5400 W Century Blvd, Los Angeles, CA 90045
    • Comfortable but nothing special – I basically lived in this hotel for several months in 2015, and it’s your basic airport hotel.
  • Courtyard King Kamehameha’s Kona Beach Hotel, 75-5660 Palani Road, Kailua-Kona, HI, USA
    • Comfortable hotel right in the middle of Kona with a small but serviceable pool and cute outdoor dining/drinking area
  • The In-Laws’ House, Volcano, HI
    • They were our reason for this trip, so why wouldn’t we stay with them?

• Eat/Drink
  • Costco, 73-5600 Maiau St, Kailua-Kona, HI 96740
    • We definitely stopped here to pick up groceries for the fam – and in the process re-affirmed why we love Costco (cheap bacon, lots of spam, and many other things)
  • Cham Cham Korean BBQ, 421 Kalanikoa St # 102, Hilo, HI 96720
    • Try and set aside your mainlander idea of timing and prompt service. I’m pretty sure we waited a half hour to get our food and it was both tasty and satisfying.
  • Volcano Thursday Night Market (hosted at the Cooper Center in Volcano Village), 19-4030 Wright Rd, Volcano, HI 96785
    • This gathering brings together food and crafts in a cute little community center – I recommend the tacos in the truck outside or the homemade pizza inside (but be prepared for a wait!)
  • I’m Happy Dough, 15-2714 Pahoa Village Rd. L3, Pahoa, HI 96778
    • Charming little vegan donut shop that set up at the Volcano market (above)
  • Punalu’u Bake Shop 95-5642 Mamalahoa Hwy, Naalehu, HI 96772
    • Get here early and get their malasadas. A consolation prize is their Portuguese sweet bread.
  • Ohelo Café 19-4005 Haunani Rd, Volcano, HI 96785
    • Make reservations if you plan to dine here, but if you do it spur of the moment, you should be able to have drinks outside with no issues.
• See/Do
  • Kipuka Puaulu, Mauna Loa Rd, Volcano, HI 96785
    • If staying in or near Volcano, I highly recommend this easy hike to get out and into nature!

Trip Background

We make at least one trip to Hawaii each year to visit my sister-in-law and her family and this year we found tickets that got us away from Chicago in February. Don’t get me wrong – I love snow. I love winter as a season in which to snuggle up with your hot chocolate and puffy jackets. But by February each year, the sub-freezing temperatures and our inability to get outside and go for walks have usually driven us mad. Especially since both of our kids are outdoor creatures and need that time outside the house.

Always pack a pair of peanut butter and jelly sandwiches. They travel well, they fill you up, and they’re excellent for pacifying two kids under four. And if needed, have a gin and juice in the airport lounge. That helps too.

Day 0 (February 19, 2023)

Our journey across the world began by heading to O’Hare Airport and to our standard first stop – the Admirals Club. The kids’ room here is really a lovely place to wait before a flight, as Caitlin and I can get a coffee or a cocktail and some snacks, while the kids can eat and run around.

One highlight from this part of the trip – the amazing gate agent helped carry our double stroller down the jet bridge for me, allowing us to focus on carrying our bags and the kids. THANK YOU, DUDE.

Clementine could have sat on our laps but we decided that she needed her own seat for our sanity. We also experimented with a new seating configuration – putting Caitlin and the two kids in the A-B-C seats on the left side of the walkway and me in seat D on the aisle. Because we sat in the last row before the exit row, there was only one seat to my right and thankfully it was empty, so Clemmie had a chance to come sit with me.

The flight to Los Angeles was relatively uneventful, and arriving around 11 PM made us a bit nervous after our previous trip to Hawaii resulted in a late-night LAX arrival and us having to schlep two car seats plus all our gear out of the terminal and to a nearby hotel. This time, our driver from the LAX Westin picked us up reasonably quickly and we were off to get a good night’s rest. Along the way, I got an offer from American Airlines on their app to give up our seats in exchange for compensation. My in-laws went to Hawaii last December (2022) and decided to take their trip as planned in spite of a $4000 per person offer – which I thought was just insane.

Day 1 (February 20, 2023)

Now I stayed at this hotel for months during a consulting project years ago and I found it comfortable – but nothing remarkable. We got some coffee and a light breakfast for the kids, then loaded up and headed back to LAX to check our bags in.

It was here that we learned that Admirals Club at Lax Terminal 5 is not great for kids – there’s no kids’ room and when you have rambunctious little ones, there’s no easy way to corral them. For the flight to Hawaii, Caitlin and I flipped seats so I sat in the middle with both kids to each of my sides, and she sat on the right aisle. A combination of movies, toys, and lollipops kept these kids in check and we landed in Kona around 5 PM. A mild panic attack set in when I thought one of our bags/car seats didn’t make the connection, but thankfully all was good.

We secured our rental car and drove immediately to Umeke’s to pick up some dinner and to Safeway to get some drinks. Knowing we’d be with the family for the rest of our trip, Caitlin and I agreed to spend one night in a hotel (the Courtyard King Kamehameha’s Kona Beach Hotel)

The hotel also came with some dinner credit, thanks to a very warm and welcoming front desk agent, so I went downstairs to grab some ice cream for the kids and a cocktail before heading off to sleep. For some reason, the live entertainment at the poolside restaurant was playing Someday by Sugar Ray – not exactly what I would imagine for a duo singer and guitarist, but hey – when in Hawaii, amirite?

Day 2 (February 21, 2023)

When you’re flying from Chicago to Hawaii, your time zones are naturally off. We woke up a little after 6 AM (which still means we slept in a ton!) and headed down to the hotel buffet for some breakfast. To our surprise, the kids were cooperative while we ate, even including the ten minutes in which Caitlin had to head over to the ABC store to pick up some diapers for Clementine.

The sunrise made for a lovely background as we ate and I was especially enamored with the bread pudding they were serving. We went back up to the room to digest, then headed over to the pool for a quick bout of swimming. It was not an ideal day for a swim, with a cool, windy day testing our comfort in and out of the water.

We packed up, loaded the car, and drove to Costco a little after lunchtime to pick up some groceries to bring to my sister-in-law Casey and her husband Jack’s house. After driving across Hawaii’s infamous Saddle Road, we arrived at Casey and Jack’s place, had some dinner, and went to sleep.

Day 3 (February 22, 2023)

Our first full day with the family saw us drive down into Hilo. We originally hoped for good weather and our naïve dreams were dashed as it poured rain all over us. We did manage to stop at Cham Cham Korean BBQ to pick up a few dishes (a combo plate, fried rice, and an order of japchae (Korean glass noodles) and the smells of this delicious food wafted around the car as I drove the family back into Volcano.

This drive was pure torture as it was raining hard, I was hungry, and the smell of this food hung in the air as if to taunt me. Thankfully after the 45-minute drive, we were able to attack this food – and attack it I did.

Day 4 (February 23, 2023)

For day four, we decided to go for a morning hike at Kipuka Puaulu, a short 1.2 mile walk through a gently sloping area with plenty of trees, flowers, and plants to see. The trails are in good shape and we brought all five kids (our two kids, Casey’s three kids) with no issues.

That night, we drove to the Volcano Thursday Night Market, which is hosted at the Cooper Center in Volcano Village. Again it was pouring so we scrambled from the car into the center to see what was for sale and what could be ordered for dinner. Naturally my eyes first caught I’m Happy Dough, a small donut shop making hand crafted vegan yeast donuts. I also noticed the Mexican food truck outside, so despite the rough weather, I dashed out from under the cover of the Cooper Center to order some tacos and a burrito. There were also a bunch of charming little shops selling soaps, jewelry, and other wares here.

We got back home a little after 6 PM (when the market closes) and the kids, still on Central time zone, started to crash around 8 PM.

Day 5 (February 24, 2023)

Caitlin suggested that Cooper and I spend part of the day together so I packed a small bag and he and I jumped in the car to head to the Punalu’u Bake Shop. This is always a place I try to hit up when we visit Casey and Jack but I always time it poorly and come in the afternoon, when they are sold out of their malasadas. But this time, we arrived at 10:30 AM and despite the arrival of a large tour group, we got there well before they sold out this time.

I haven’t been able to bring Cooper or Clementine to Leonard’s in Honolulu, who make what I consider to be the finest malasada around – but that didn’t stop me from introducing the Portuguese treat to my son. He seemed to love it, but what kid wouldn’t like sugar on a fried pastry?

We also picked up some lunch plates (they didn’t have loco moco’s, but I got a hamburger steak combo plate and a chicken teriyaki plate instead). We stopped at the park across the street where Cooper in 2021 had loved the sprawling grass and slides, but this time he didn’t seem to love it. We returned home to eat our newfound bounty before he spent the afternoon running around the house and playing with his cousins.

That night, Casey and Jack offered to watch Cooper and Clemmie while Caitlin and I headed to Ohelo Café for drinks. This place offers a substantial (and fancy) menu but since we didn’t have reservations, we opted for a couple drinks and a couple hours of kid-free time. The pleasant server/bartender even made us a cocktail, asking us to try it and let us what we thought of the recipe. And he didn’t even charge us for it!

Day 6 (February 25, 2023)

The whole point of timing this trip was to be here in Hawaii for Casey’s son Boone’s birthday. There was a ton of sushi and food, beers, and cake (naturally) – and the pre-party time gave Clemmie and her cousin Maple time to bond.

By the end of the day (~9 PM), the kids were pooped – as were the adults.

On our final night in Hawaii, the rain was falling particularly hard and in waves. It came and went, for thirty seconds at a time, and the slow rumble of rain on the sheet metal roof put me at ease. It’s no wonder these meditation apps and sound machines all use falling rain – it really does wonders for helping people sleep.

Day 7 (February 26, 2023)

Whenever we depart the Big Island, I always wonder how badly the flight is going to go. And that starts with the departure time. Originally scheduled for 5:01 PM from Kona (remember, we’re in Volcano, which means we have to drive an hour east to Hilo and then take the Saddle Road across the island), the flight starts to get delayed.

We leave from Casey and Jack’s house around noon, knowing we’ll need to stop for lunch and gas and still aim to be at the airport a few hours early (we have seen nightmare scenarios of hours-long waits just to get through security).

A quick stop at McDonald’s turned into a long stop at McDonald’s as my attempt to shortcut the drive-through by going into the restaurant failed. It took us probably 20-30 minutes to get our food…oops. At least their McDonald’s have cool menu options!

We got to Kona airport at 3 PM after returning the rental car and this is where the open air airports of Hawaii shine. We let the kids run around for awhile, and in between trading off kid duty, we grabbed some food from the Kona airport restaurants.

We were boarded by 6 PM, pushing back by 6:20 PM, and soon enough we were on our way across the Pacific. The kids managed to sleep part of the way and we arrived curbside (sans the car seats and big luggage, which thankfully could stay at the airport since it was <16 hours between connections) around 2 AM.

We quickly got aboard The Westin Los Angeles Airport shuttle and got to the front desk around 2:15 AM. A quick check-in gift later and by 2:30 we were headed to a quick but much-needed night of sleep.

Day 8 (February 27, 2023)

Arising in Los Angeles, we grabbed a quick coffee before heading to the Admirals Club at LAX where we let the kids eat their snacks and play for a bit before our flight back to Chicago. I have made this statement before and I will state it again – if you travel with kids and your preferred airline is American Airlines, you have ample reason to consider getting an Admirals Club membership. Getting into one with a kids’ room is THE place to unwind as you’re in transit, and it makes the entire journey easier. Now if only they could set up a kids’ room on the plane!

Final Thoughts

Any trip to see family is usually filled with the same heartening and maddening moments that family brings. Minus my allergies acting up, this was a nice trip.

I did realize something though – certain travel accessories make it easier when traveling with little kids.

• Mirror for car: Because Clemmie sat in a rear-facing position, it would have been nice to be able to see her. Having a mirror on the headrest of her seat would have made it easier, and we have an extra one at home.
• Dash camera: We bought this one a couple years ago when we got our new car and it’s a huge relief to have this always on, just in case.
• Phone Holster/Belt Case: When you have kids in one arm, it helps to have a place to put your phone besides your pocket. I bought this model when I switched to the iPhone 13 Pro Max and it’s great to not have the phone bulging out of your pockets.
• Beach bag (collapsible backpack): I have a different Eddie Bauer bag, but this 10L packable sling is perfect to bring on trips – you unpack it and throw stuff in for a quick day trip or beach adventure.
• Tiny vaseline: great for small cuts and chapped lips.
• Kindle: When you kids commandeer your ipad, have your Kindle handy.
• Sock with two tennis balls – I happened to read this article while en route, and the idea of relieving the back pressure one gets from long flights sounds pretty good to me!
• Body wash: don’t assume you’ll find the brand you want. Bring what you know you know!
• Travel scale: I bring this scale on virtually every trip in which we need to check bags, and doing so has prevented me from paying excess weight luggage fees.

If you’re planning for a trip with little ones coming up, keep these in mind!