TL;DR

Volcano/Hilo

• Stay
  • The In-Laws’ House, Volcano, HI
    • Nothing beats free lodgings and time with family! 🙂
  • Volcano Red Sky tea garden, 99 Kanawao Pl, Mountain View, HI
    • If you need proximity to Volcanoes National Park and a very chill Airbnb, this is it. Heather and her family will be lovely hosts.
• Eat/Drink
  • Poke Market, 41 Waianuenue Ave, Hilo, HI 96720
    • Just a delightful lunch. Parking is a bit dodgy but the meal is WELL worth the effort.
  • Suisan Fish Market, 93 Lihiwai St, Hilo, HI 96720
    • Always a staple visit for us when we see the family in Hawaii. Pick anything and you’ll enjoy it. But don’t buy a tank top thinking the sizes are for men – I learned this the hard way.
  • Ken’s House of Pancakes, 1730 Kamehameha Ave, Hilo, HI 96720
    • The kind of diner that you’d recognize in any small town, but one I continue to visit each time we go to Hilo. I got the corned beef hash moco (loco moco with hash) and it was delish – but heavy!
  • KTA Super Stores – Downtown, 321 Keawe St, Hilo, HI 96720
    • Where you should shop for groceries if you’re in Hilo
  • Hilo Farmer’s Market, Corner of Kamehameha Avenue and, Mamo St, Hilo, HI 96720
    • Super charming marketplace with so many different kinds of fruits and vendors selling crafts and wares.
  • Kula Shave Ice, 57 Mamo St, Hilo, HI 96720
    • Located inside the Hilo Farmer’s Market, this little gem will give you a cool, sweet treat to cool down with.
• See/Do
  • Kilauea Overlook
    • It’s a view from up on high, and worth visiting for the majestic beauty. On a gray, cloudy night like the one we visited on, it was a little less grand.
  • Liliʻuokalani Park and Gardens
    • A beautiful place to sit and eat lunch in downtown Hilo – find the benches by the water and enjoy your meal with the soothing lapping of the waves against the shore.

Waikoloa/Elsewhere

• Stay
  • Hali’I Kai at Waikoloa / Live Hawaii-Style! Ground Floor Lanai w/Grill, Kitchen, WiFi, AC–Halii Kai Waikoloa 4E
    • This was our home away from home – and while it was nice, it was not designed for kids. There was one couch and one terribly uncomfortable chair for four adults and four kids – and they had a glass coffee table. Not ideal! But comfortable bedrooms for sure.
• Eat/Drink
  • Ocean Club at Halii Kai, 69-1029 Nawahine Pl, Waikoloa, Island of Hawaii, HI 96738-5748
    • Attached to the pool at our Airbnb (basically a gated community) was a wonderful bar and restaurant which we frequented almost every day!
  • KTA Waikoloa Village, 68-3916 Paniolo Ave., Waikoloa Village, Hawaii 96738
    • If you’re staying in Waikoloa, you might need groceries. And if you do, you need to come here.
  • Sun Dried Provisions / Kona Grill House, 81-951 Halekii St., Kealakekua HI, 96750
    • If you’re passion through, stop here for their delicious poke.
  • Punalu’u Bake Shop, HI-11, Naalehu, HI 96772
    • We tend to stop here on every trip to the Big Island. If you do come here at the end of the day, don’t expect to find much. There’s a reason they sell out of things! Come here early enough and you will get to buy their delicious sweet bread!
  • Leahi Market, Honolulu International Airport
    • I enjoyed the kalua pork here!
• See/Do
  • Anaehoomalu Beach (A-Bay”), 69-275 Waikoloa Beach Dr, Waikoloa Village, HI 96738
    • This is where you can come for a few hours, ideally with a small tent, a wagon, and a cooler full of drinks and food – and let your worries float off into the blue sky.

Trip Background

Some of you might know that I have a special place in my heart for Hawaii. As a kid, my parents would take me every summer until it became hard for my mother to fly – which meant that eventually, it was my Dad taking just my sister and me. And soon enough, we just stopped flying to Hawaii completely because I was heading off to college and things were just changing in our lives.

But my connections to Hawaii had always run deep and would continue to do so. My great-grandfather was born in Hawaii in 1903. My mother had grown up for a time in Hawaii. And after college, my best friend got a dental residency in Maui. So when my sister-in-law Casey and her husband Jack moved to the Big Island in 2014 (so he could take a job at Volcano National Park), my then-girlfriend/now-wife Caitlin and I knew we had a natural reason to visit (that pun was unintended). This reason became all the more important when Casey and Jack had the first of their three kids in 2015. We had planned to visit them all last spring after the birth of their third child Boone, but covid-19 obviously derailed those plans.

Back in January 2021, American Airlines sent me an email notifying me of a fare sale as part of a broader series of promotions they were running. I curiously clicked to see what was on sale and to my delight, I found a $99 one-way ticket from Chicago’s O’Hare International Airport (ORD) to Honolulu (HNL).

$99.

One way.

That is just insane.

So after a quick consultation with the wife and discussing the risks, we decided to take a chance and buy three tickets, knowing that we could always cancel them later on since the major airlines had done away with change fees. I ran into two annoying issues resulting from I used flight voucher credit from 2020’s canceled trips – basically, it took longer to confirm the tickets than I would have liked, and then after numerous emails and delays involving promised paper vouchers for the difference, I still never received a paper voucher. Thankfully after another email, I received a digital voucher … honestly why even use paper vouchers anymore?

But the story that defined this trip was not the ridiculously cheap tickets. Rather, it was our adventure in complying with Hawaii’s Safe Travels program requirement and getting our tests done on time that created tremendous anxiety.

We initially chose Walgreens because it was free. Knowing we needed a test within 72 hours of our departure TO Hawaii and with a Monday morning flight scheduled for 10:30 AM, we scheduled our tests for Friday morning. But the Walgreens pharmacist told me that their lab doesn’t analyze tests on weekends because they’re a Monday-Friday lab. So then what we were to do?

We opted to drive to CVS immediately (by now it was Friday at 11 AM), pay the $139/person fee, and were told we would have the results within 1-3 days.

At 2:02 PM on Saturday, March 27, CVS sent me my results. Caitlin’s test completely upended our world.

Her positive test was surprising because she had isolated, had virtually no contact with anyone outside our home, and had no symptoms. She had to scramble to CVS to get a second test at 2:40 pm on Saturday. The rest of Saturday she isolated herself downstairs away from me and our son, just in case the test was accurate. The same all-day Sunday, by which time we had both resigned ourselves to the possibility that we weren’t going to Hawaii. The results came in at 9:36 pm on Sunday, March 28. This time thankfully it was negative.

Her Walgreens test came back at 9:16 pm on Sunday. Pretty good turnaround time considering we’d submitted it only 36 hours earlier. But with a negative test in hand, a flurry of activity went off in our home as we finished packing all of the “day of” stuff that we had yet to assemble.

Day 1 (March 29, 2021)

Our flight to Honolulu took off at 10:35 AM so we decided to take a Lyft to Chicago’s O’Hare International Airport a few hours before our flight. Getting to the airport was a little nerve-wracking (the first time we’d been in a rideshare in a long time) and waiting for our flight to take off was definitely a nervous feeling, as we had not been in an airport in a long time.

The nine-hour direct flight to Honolulu had us worried because it would be the first time we would fly since the pandemic took hold. And with our son Cooper, we anxiously hoped he would be good the entire journey. Since he was not yet two years old, we also knew this would be our last flight without a mandatory mask for him, so off we went with our fingers crossed.

The journey was surprisingly good. Cooper watched Frozen and Moana, we took turns reading or napping, and we landed in Honolulu with no real problems. They did awkwardly ask us to move Cooper from the middle seat to the window though (apparently it’s not allowed) – but it seemed like there was an inconsistent application of said rule that a child seat could not be in the middle or aisle seat. Also, I did have a momentary freak out when I looked out onto the wing and saw what I thought was duct tape everywhere – but I have since read Patrick Smith’s Cockpit Confidential which specifically addresses this question, and learned that this is speed tape, a heavy-duty aluminum bonding tape. Basically, nothing to worry about.

Upon landing in Honolulu, going through the health evaluation process was a little tricky. We waited in a long line with all of our documentation and as soon as we passed through, we had to hustle to the baggage claim to grab our bags, transfer them from American Airlines to Hawaiian Airlines, and go back through security for our connecting flight to Hilo.

This flight was considerably easier (and the flight was super empty). We landed and waited about an hour for my sister-in-law Casey to pick us up – which she did, along with these delicious poke bombs she had bought at the store. Gotta love the Aloha spirit you only get from family!

Day 2 (March 30, 2021)

I had a realization. When I come back to Hawaii next and if I want to do an early morning sunrise hike, coming from the Midwest or east coast makes that super easy. I was up at 3:30 AM so I could be on work calls, and because that’s 8:30 AM central time, I was able to get up with minimal effort.

The problem with working in Hawaii while supporting a midwestern time zone is that getting up at 2 or 3 AM really messes with your sleep patterns. I spent the first full day working from the Airbnb my sister-in-law had rented for us, then crashed around 7 PM local time as my jet lag slowly began adjusting. So…yeah, that was basically a wasted day. 🙂

But Caitlin and Cooper had a nice day of playing with Cooper’s cousins!

Day 3 (March 31, 2021) – More work…ugh

Day 3 and Day 2 were alarmingly similar. A beautiful morning as captured by some of these photos, but an afternoon spent walking around the neighborhood, playing with the kids, and nothing touristy.

The evening though, provided a lovely change of pace, as Casey offered to watch Cooper for a couple hours so Caitlin and I could wander out of the house. We decided to drive to the Kilauea Overlook and hike for an hour. Most folks were respectful and wore masks when they saw others.

To our surprise, there were probably 50-70 people there when we arrived and by the time we were ready to leave, there was a line of cars waiting to enter the parking lot.

Day 4 (April 1, 2021)

Day 4 saw our first daytime adventure beyond the neighborhood. We decided to put Cooper in the stroller and take a long winding walk down to the Kilauea Military Camp (KMC), a facility right next to Volcanoes National Park that is open to members of the military and their families.

We weren’t staying there but instead went to the park so the kids could play and I wound up having a lovely hour-long conversation with a woman named Christina, whose kids were also at the park. She had gotten marooned in Hawaii trying to get to New Zealand when the pandemic started and because they couldn’t proceed onward, they opted to remain in Hawaii. We had a really interesting dialogue about race in America, life in and after the pandemic, and shared experiences (she was a chef who had lived all over the world). These are the kinds of memories that fill my heart with joy – meeting new folks and having serendipitous moments of conversation in far-off places.

After the kids played for a couple hours, we stopped at the KMC General Store for some sodas and snacks, walked home, and enjoyed the rest of the afternoon watching movies and playing with the kids.

Day 5 (April 2, 2021) – The Vacation Begins

Okay. So by now, you’re thinking…jeez dude. Did you travel all the way to Hawaii just to work and watch the kids? Heck no! With my morning meetings complete, we packed our bags into the car and departed from Volcano eastward down to Hilo for lunch before we would head off to our destination for the next few days: Waikoloa.

Our first stop was Poke Market to grab some poke bowls for lunch. We pulled off to the side of the road to enjoy a leisurely lunch then started our convoy rumbling toward Waikoloa.

Okay, now for a more serious message…

Whereas Kona feels touristy, Waikoloa feels less so. I mean, don’t get me wrong. You know it’s all visitors coming to their second homes or the Airbnb’s/VRBO’s they’ve reserved for time away, but it doesn’t feel like all of the local businesses are just there to serve tourists. Prime example: the Ocean Club at Halii Kai was the pool and restaurant/bar attached to the place we were staying. And the service was wonderful. The staff was incredibly engaging and the food and drink hit the spot after a long afternoon of swimming in the Hawaiian sun. And as if our day wasn’t charming enough, whales were breaching off the shore as the sun was setting. Simply wonderful!

The splendor of whales in the Pacific Ocean

Day 6 (April 3, 2021) – Lazy Pool Day

You’re going to start to notice that my descriptions of what we did start to get a little thin in detail here. That’s because you can only say “we swam, we sat by the pool, and ate fries” so often. Our first full day in Waikoloa began with the pool in the morning and ended with pool in the afternoon. Lunch was taken at the poolside – and with our son plus my three nephews and nieces, fries were the order of the day.

In fact, the only time we left the property was to get groceries at KTA Waikoloa Village – which if you stay here will be the best place to pick things up.

Day 7 (April 4, 2021) – Real Beach Time!

Day 7 seems like a bit of a misstatement. I mean, working while in paradise (for four days) really wasn’t the brightest idea on my part. But the good news is that day 7 of our Hawaiian trip brought us to Anaehoomalu Beach (A-Bay”) – a proper beach. We started the morning by filming a small announcement (that we were expecting our second child – a girl!), then spent the majority of our day swimming, napping in the sun, or playing with the kids in the sand.

Returning to our rooms, it was clear that ice cream was a popular decision. As the afternoon approached, we decided to go for a short walk along the coast near the Hilton Waikoloa Village. It actually brought back a flurry of memories as I had stayed here once as a kid when I went on vacation with my Mom and Dad ~30 years prior. Seeing the waterfall, the shops, and the attractions made me wish (a little) that we’d stayed at a proper hotel. The good thing about that hike is that gave us a chance to see the sunset from a different angle – and really, are there any bad ways to watch the sun set on a Hawaiian day?

We returned home and I had a moment of nostalgia thanks to my grocery run the previous day to KTA. There I found a box of It’s Its, which is really one of the best ice cream sandwiches you’ll ever find. Founded in San Francisco, it brought a wave of nostalgia over me, and then I promptly devoured one – much to my son’s jealous displeasure. Don’t worry – he got one too.

We ordered take out which my wife Caitlin went out to get – and unfortunately, due to the restaurant’s staffing issues, it took her over an hour to get the food and bring it back. Suffice it to say, we were all hungry by the time she returned and ate our dinner quickly and in silence as a result.

Day 8 (April 5, 2021)

The morning pool routine really makes a kid happy – and his parents. By the time we returned to the house for lunch, the little man was hungry and his chip-crumb-covered face should be evidence of how he responded when we put his lunch in front of him.

Returning to the pool for another afternoon was made even better with a strawberry daiquiri to enjoy with our sunshine.

On our last night, we decided to make it easy and avoid another takeout fiasco and had our dinner by the pool.

Day 9 (April 6, 2021)

Our final day in Waikoloa arrived and how did it start? Yoga on the beach? Morning cocktail? Saw a whale?

No. We cleaned up the house cause it’s an Airbnb. And four kids leave a lot of destruction in their wake. So after cleaning and restoring the house to its original state, we packed the cars and loaded up for the drive back to the other side of the island.

We tried stopping at a place called Rebel House – I’m not even going to link to them because their service was crap. They basically refused to serve us – so we left. We stopped instead at Sun Dried Provisions – and holy moly was that some amazing poke. If you go check out their website, they have a video of how the chef preps the poke. We took our tasty lunch to Pu’uhonua O Hōnaunau National Historical Park – don’t forget your “America the Beautiful” National Parks card if you have one. And if you don’t have one, consider it – it will get you into every national park as many times as you want in a year!

Top left – Sun Dried Provisions, Top Right – The damned good poke, Middle Right – Dining on the park bench, Bottom – the beach at Pu’uhonua O Hōnaunau National Historical Park

Along the way back to my sister-in-law’s house, we stopped at two places: Punalu’u Bake Shop (where I sadly discovered that at the end of the day, all of the good pastries and all of the sweet bread are GONE), and Naalehu Park (so Cooper could get out and run around for a bit before we went home).

That night after Cooper had gone to sleep, I looked back on the following words, which I had written when we were at Pu’uhonua O Hōnaunau National Historical Park. They were the ramblings of someone who had been cooped up (pun unintended) at home for far too long with too few social interactions and vacations:

There is something remarkably refreshing about the sea breeze off the Pacific Ocean. The kind that drowns you in the cool air that feels moist and reminds you that you’re on vacation – as if the hot sunshine, the smell of suntan lotion or coconut oil, or the full belly of fresh poke doesn’t adequately do the job.

I’ve been here nine days and after finally acclimating to the time zone change, not having to work central hours anymore, and having time to swim, sleep, read, learn, and chill, I am finally at ease. It’s one of those inevitable cruelties of travel that just as you’re getting used to a place, you have to leave. But an idea sprung forth from my latest audiobook (Drive) that is starting to grow like a seed firmly planted in soil with enough water and sunlight to germinate.

What if we abandoned our jobs for a year, took Cooper to another part of the world, and just lived? Put our stuff in storage, let a nice family who wants to transition to the north shore (of Chicago) move into our house, and let them cover the mortgage while we head off to parts both known and unknown?

I still these about these words a year later and how one day we might be able to make this a reality while not forfeiting our financial security. I don’t have the answer (yet) but I do know this will happen one of these days!

Day 10 (April 7, 2021)

Our last full day in Hawaii came with a lovely fresh breeze, both figurative and literal. My sister-in-law agreed to watch Cooper and gave Caitlin and me a few hours to drive down into Hilo for a day-date and some time off – which was a wonderful way to end our last day.

Anytime I drive into Hilo, I try and hit up two places: the Suisan Fish Market for their simply wonderful assortment of poke and Ken’s House of Pancakes for their loco moco and other plate lunches (and because I get the feeling it hasn’t changed much over the decades it’s been around). Both of these places bring a touch of nostalgia as places they have survived and still deliver amazing food to their customers. Ken’s, in particular, reminds me of a place I used to go to in Honolulu when my family and I would take our annual summer trip to Hawaii. That place was called Liki Liki Drive-In, and maybe I am just nostalgic for times long passed, but I love diner-style restaurants.

We took our food to the local Liliʻuokalani Park and Gardens and enjoyed a casual picnic on the tables by the water. It was the first time all trip that we did not have a child nearby – and we relished the absence of kid-induced insanity, the sounds of the water lapping against the rocky shore, and the smell of the breeze off the Pacific.

Afterward, we stopped by KTA Super Stores – Downtown to pick up some groceries for the family and some snacks for our flight home. We would have gone home from there but something about the Hilo Farmer’s Market beckoned to us. So after buying a shave ice bowl and an acai bowl from Kula Shave Ice, we wandered through the marketplace (where I bought a cheeky spam musubi dishtowel) before heading back to my sister-in-law’s house.

Day 11 (April 8, 2021)

One of the most difficult things to do in Hawaii these days is getting a ride. It’s not like you can just grab an Uber or Lyft and expect a driver to show up within 10 minutes like we get at home outside Chicago. Thankfully in-laws had an extra car and were amazingly generous. They let us take their car to the airport, where we parked it and my brother-in-law would come by later with his keys to bring it back to their house. Remind me to send them a gift for that little extra bit of aloha spirit.

Our time at the Hilo airport and the flight to Honolulu was easy. Hilo’s open-air waiting areas make it so easy to wander and enjoy the fresh air while waiting for one’s flight. Because we took Southwest to HNL and were continuing onto an American Airlines flight to O’Hare, we had to transfer our luggage ourselves. Having a kid, car seat, stroller, and all your gear makes you realize how much stuff a family needs to pack to be able to go anywhere.

After we arrived in Honolulu, transferred our luggage to American Airlines, and got our boarding passes, we attempted to go through security but ran into a small (actually significant issue). Apparent someone pulled a fire alarm, which resulted in the TSA closing one checkpoint. A massive line formed for the only open security area that had to have 200+ people in line. At one point, the closed security area re-opened, and everyone in the back half of the line b-lined for the now-open checkpoint.

There aren’t many airports at which I would enjoy taking a connection – but Honolulu’s Daniel K. Inouye International Airport is one of them. For the most part, we were very comfortable here. When you have a toddler who needs to run, having outdoor areas is a godsend. We sat down at the Leahi Market for a meal which was also quite good. Sadly this is where our good travel experience ends.

Let’s just put it this way – this was the WORST flight experience I have EVER had. We lost Cooper’s sippy cup in transit, my poor son did not adjust well to the air pressure, and it was a red-eye. He cried almost the entire way home. And to top it off, three irritating women who sat in front of us set the tone for the flight by mumbling “Well I guess we’re not going to get any sleep on this flight” before we took off – after they saw my son. I understand that flying near a toddler or baby is not ideal, but to those three women, “F*ck you.”

Clearly, they weren’t parents, empathetic, or looking for good karma. I enjoyed the fact that they had a lousy flight home too because they displayed no compassion whatsoever. Sheesh, and here I thought a trip to Hawaii was going to lower my blood pressure.

Final Thoughts

We landed at O’Hare having barely slept at all. Either my wife or I was carrying our son up and down the aisles while he bawled for the entire flight. We arranged an Uber, rode home, and found my wife’s parents at our house having set up streamers and cake for my wife’s birthday. It was incredibly thoughtful but all I could muster was, “Can you watch Cooper for a few hours?” They graciously accepted while I turned and fell onto the couch – where I would not move for a good four hours.

This was one of those trips where I realized that trying to work while in Hawaii is not ideal. The time difference makes 3 AM wake-up calls particularly jarring for anyone based in the central time zone. And quite frankly if you’re going to see family, see your family! Don’t work! Lesson learned.

We try to go to Hawaii once a year so my wife can see her sister and all the kids can see one another. And this trip reminded me once again of the importance of proximity to friends and family. And even though it has taken me 15 months to complete this write-up, I’m already feeling like it’s time to head back to the islands.