TL;DR

En Route

• Stay
  • Sheraton Gateway Los Angeles Hotel, 6101 West Century Boulevard, Los Angeles, CA, USA, 90045
    • We decided on a longer layover so Cooper could swim and both kids could rest – and although this adds time and expense, it’s so much better for our kiddos.
  • Four Points by Sheraton Los Angeles International Airport, 9750 Airport Blvd, Los Angeles, CA 90045
    • DO NOT STAY HERE. There are better hotels, but also their shuttle did not pick us up and multiple calls to the hotel did not yield any action. Only because we were lucky and another hotel shuttle driver took pity on us did we get to our hotel (with all our luggage and car seats, cause we had to take it out of the airport)
• Eat/Drink
  • The Admirals Club in Terminal 3 (Concourse H/K), 10000 W Balmoral Ave, Chicago, IL 60666
    • The kids area by itself makes an Admirals Club membership worth it

South Shore/West Shore/East Side of Kauai – basically everything but the North Shore

• Stay
  • Koloa Landing Resort at Poipu, Autograph Collection, 2641 Poipu Road, Koloa, HI, USA, 96756
    • This resort blew us away. We originally booked a single bedroom with a pull-out couch, but at check-in, the front desk agent smiled and informed us we had been upgraded to a two-bedroom villa! See the video below!
• Eat/Drink
  • Holoholo Grill, inside the Koloa Landing Resort at Poipu, Autograph Collection, 8581, 2641 Poipu Rd, Koloa, HI 96756
    • If you stay at Koloa Landing, you will likely eat here on multiple occasions. We did and we were very satisfied with both the delicious breakfasts, afternoon poolside snacks, and dinners!
  • Midnight Bear Breads, 3830 Hanapepe Rd, Hanapepe, HI 96716
    • The smells of baked bread and pastries will tackle you like a defensive end – and then give you a bear hug of joy. Try that macadamia nut cinnamon roll and the nutella cruffin. Oh my.
  • Japanese Grandma, 3871 Hanapepe Rd, Hanapepe, HI 96716
    • Book well in advance for dinner here. The outdoor seating area out back is super charming and their food is excellent. Don’t hesitate to try a variety of rolls or sashimi – and two of their cheesecakes (matcha and strawberry) were to die for.
  • Chalupas, 3477 Weliweli Rd, Koloa, HI 96756
    • Did I go all the way to Hawaii and then order Mexican food from a food truck? Yeah. And was it good? Eh. But we were hungry and had two tired kids.
  • Big Monster Sushi Food Truck, 3477 Weliweli Rd, Koloa, HI 96756
    • Yeah after I ordered mexican food, we got some sushi.
  • Kokee Lodge, 3600 Kokee Rd, Waimea, HI 96796
    • A lovely little find after exploring the Waimea Canyon State Park. Great place to both eat some lunch, listen to some music and let the kids run around in a giant open field for awhile.
  • Koloa Fish Market, 3390 Poipu Rd, Koloa, HI 96756
    • You can do no wrong here. Literally. Pick any combo – just make sure you also pick up some mac salad, seaweed, and some spam musubi on the side. Oh and kalua pig with rice!
  • The Right Slice, 2-2459 Kaumualii Hwy, Kalaheo, HI 96741
    • This charming pie shop serves both sweet and savory. We’d driven by it four or five times by the time we came by. We took him both sweet pies, a chicken pot pie (which we baked in our kitchen), and a cute little mug
  • VIP Treats and Sweets, 4-831 Kuhio Hwy Ste 439, Kapaʻa, HI 96746
    • This place was closed due to the owner being on vacay, and I cried. I needed malasadas bad.
  • Haole Girl Island Sweets, 4-369 Kuhio Hwy, Kapaʻa, HI 96746
    • Simply delicious. A few highlights/recommendations: the pear/fig/almond franchipan, the ube with coconut, char siu, lilikoi passionfruit curd with cream cheese filling, and the taro coconut muffin. You also cannot go wrong here.
  • Hamura Saimin, 2956 Kress St, Lihue, HI 96766
    • Cash only, hole in the wall. Super tasty and if you have the option, go dine in. These kinds of places don’t exist anymore, and while you CAN eat it in your car or at the beach, this food is best served and consumed in house.
  • Aloha Sweet Delights (or Delites, depending on who’s asking), 12550 Kaumualii Hwy, Kaumakani, HI 96747
    • Bakery on the way west to Waimea Canyon State Park (or back east from Kekaha, depending on where you’re coming from) with malasadas (yesss) and plenty of other baked goodies
  • Wong’s Chinese Restaurant, 13516 Kaumualii Hwy, Hanapepe, HI 96716
    • To be honest, I stopped here because I heard they serve proper plate lunches – and my locomoco was tasty and affordable.
• See/Do
  • Hanapepe Art Night, Hanapepe Rd, Hanapepe, HI 96716
    • Super charming gathering of vendors selling their art – only happens on Friday nights. My advice: get there early to browse, maybe have a snack at Midnight Bear Breads, and see if you can time it to have dinner at Japanese Grandma’s. We did not plan these together so we came back the following night for dinner (was still good!)
  • Poipu Beach Park, 2179 Hoone Rd, Koloa, HI 96756
    • A great place to spend the day. Bring a blanket, towels, and your picnic items. Also there may be turtles (honu!) sleeping on the beach. DO NOT TOUCH THEM. Don’t be THAT tourist, please.
  • Hanapepe Swinging Bridge, 3857 Iona Rd, Hanapepe, HI 96716
    • Not gonna lie – I have a fear of heights. This bridge exacerbated that in me. But the views are quite lovely here and it’s worth walking the bridge to see those views. Maybe next time without two tiny kids, though.
  • Waimea Canyon State Park, Waimea Canyon Dr, Waimea, HI 96796
    • I didn’t realize this was considered “the Grand Canyon of the Pacific,” and as you proceed further into it, you understand why. Simply breathtaking views (assuming the fog and clouds clear) – and even if they don’t, it’s still marvelous. What follows are each of the lookouts you can stop at.
  • Waimea Canyon Lookout
    • Your first stop as you venture into the park will yield multicolored hues of brown and green and gasps of “ooo”‘ and “aaah.” There’s a decent-sized parking lot here – pay for your parking and place the ticket on your dash before going to the lookout itself. Also consider using the restrooms here.
  • Waipo’o Falls Lookout
    • More oo’s and aah’s
  • Pu’u Hinahina Lookout
    • More oo’s and aah’s
  • Kalalau Lookout
    • Okay, THIS is the stunner. I’m not ruining any surprises. Any Google search or even the link here will reveal that it’s “one of the most-photographed and well-recognized valleys in all of Hawaii.” And for good reason.
  • Pu’u O Kila Lookout
    • Oh wait, you thought it couldn’t keep going and get better? BOOM.
  • Niihau Lookout
    • You’d want to have binoculars or a telephoto lens to see an island you can’t go to (only 17 miles away).
  • Kauai Coffee, 870 Halewili Rd, Kalaheo, HI 96741
    • I mean, yes, it’s a touristy place. But a nice placed to get a coffee (iced if it’s particularly warm), buy some coffee to bring back, and to talk through the fields in their charming tour path (self-guided) with cheeky signs.
  • Lydgate Beach Park, Leho Dr, Lihue, HI 96766
    • If you’re coming here, stop by Haole Girl Island Sweets or another place nearby to get some food first, then come here. It’s a lovely place to swim with kids.
  • Kauai Plantation Railway, Depot, 3-2087 Kaumualii Hwy, Lihue, HI 96766
    • This is where we discovered Cooper loves trains (riding on them). $57 for four of us wasn’t cheap but it was a charming ride and you get to feed the animals too!

North Shore of Kauai

• Stay
  • Our VRBO at the Cliffs at Princeville, Unit 7301, 3811 Edward Rd, Princeville, HI 96722
    • Beautiful views of the Pacific from this unit (which was on the top floor) and plenty of space, but the age of this unit showed. When we plugged one light into the outlet, it blew the fuse. The outlet, the vacuum cleaner, and some of the features are straight from the 1980’s. Maybe even before that.
• Eat/Drink
  • The Hanalei Gourmet, 5-5161 Kuhio Hwy space 5, Hanalei, HI 96714
    • The day we came here, we were sweaty and tired. We had spent the morning at Ha’ena State Park, there was a terribly long delay in the bus getting us back to our car, and we were grouchy. The food here settled some of that grouchiness for sure.
  • Pat’s Taqueria, Black Pot Beach, Hanalei Pier, Hanalei, HI 96714
    • You went to two Mexican restaurants while you were in Hawaii? Yes, but this one was pretty good. We didn’t get to savor the food as the kids were being fussy, but you can bring your food to the long Hanalei Pier at Black Pot Beach for some stunning views.
  • Pink’s Creamery, 4489 Aku Rd, Hanalei, HI 96714
    • This charming little shop has a number of tasty flavors, but the Mango and Cream was … ::does the chef’s kiss hand gesture:: delish!
  • Big Save Market, 5-5172 Kuhio Hwy, Hanalei, HI 96714
    • If you need groceries, come here. This market is inside the Ching Young shopping center, so parking is a bit dodgy. But a great place to load up.
  • Holey Grail Donuts, 5-5100 Kuhio Hwy, Hanalei, HI 96714
    • Whoa whoa whoa now. This is the one MUST go-to place on the North Shore. I recommend getting a box with several flavor options – I got Saffron Snickerdoodle, Shamma Farms (calamansi, a kumquat-citrus hybrid fruit grown primarily in Asia)Chocolate Crunch, and Miso Honey (This is what I wrote the moment after I took the first bite: “it tastes like what God‘s version of French toast with a sprinkling of black sea salt might taste like.”)
• See/Do
  • Ha’ena State Park,  6CC9+8R Wainiha, Hawaii, Kapaʻa, HI 96746
    • BEAUTIFUL. But caveat – we only went as far as Ke’e Beach as we had the two kids with us but you can hike the Kalalau Trail if you want (permit needed). Either way, see below in the “some important callouts before you leave” section on how to book your visit at least 30 DAYS IN ADVANCE. No joking on this.
  • Hanalei Valley Lookout, Kuhio Hwy, Princeville, HI 96722
    • Stop here on your drive and look out upon what might pass for Vietnam or another southeast Asian country. Splendid paddies and fields in the shadow of the mountains will awe and inspire.
  • Kilauea Lighthouse, 3580 Kilauea Rd, Kilauea, HI 96754
    • We attempted to go here but we needed reservations we did not have. Lesson learned – make reservations.
  • Anini Beach
    • The most secluded beach we went to the entire time. There’s not a lot of parking so I recommend going early.
  • Hanalei Pier, Hanalei, HI 96714
    • Head all the way to the end, then turn back and see why this place is legendary.

Trip Background

In May 2022, I discovered a nice deal – $552 per person for us to fly from Chicago to Lihue, through Los Angeles on American Airlines. I’ve been to Hawaii many times in my life but had never been to Kauai and I was eager to visit it for the natural beauty. We also knew that with Clementine approaching her first birthday (in the fall) that we wanted to travel with her as a lap child while she was small enough to handle.

So I started planning out what we wanted to do on the island and eventually, we settled on five full days in Koloa and on the south/west sides of the island and three full days on the North Shore (Princeville area).

I don’t have a lot of shame in buying guidebooks for I find them a helpful way of looking at the larger space (the island of Kauai) while also providing rich context on things to do, see, and eat. If you feel so compelled, check out the Lonely Planet Kauai 4 guide!

Day 0 (August 25, 2022)

Our journey to Hawaii began by taking a Lyft to ORD with a super helpful driver who helped us both load and unload all of our gear. Because we have two kids, that requires us to pack a lot of gear – a stroller, a Lille baby carrier, and diapers…oh so many diapers.

God bless curbside check-in as we were able to check all of our gear in without having to lug it into the terminal. Our first stop for virtually all flights (assuming we have the time) is the Admirals Club in Terminal 3 (Concourse H/K) where we loaded up on coffee and water for the kids.

Then something happened which, albeit a rare occurrence, is super frustrating. The American Airlines app indicated the flight was delayed, so we decided to kick our feet up to wait. Then without warning, it was moved back up to its original departure time so we had to haul ass out of the lounge and down to the gate.

The flight to LA was relatively easy as we turned on the Kindle Fire with its kids’ games – and that was a fun realization that the kids could be placated by some simple screen time. Now we are not fans of the idea of our kids being glued to technology, but thankfully this is not the case for two reasons:

1. Our kids prefer non-screen time, especially beach/pool/outdoor activities.
2. And screen time on planes is perfectly reasonable when taking a long set of flights (like we were doing)

Our outbound flight landed in LA and had a seven-hour layover, we decided to take the kids to the Sheraton Gateway Los Angeles Hotel so they could swim, get some energy out, and sleep. The free airport shuttle was easy to pick up (and thank goodness we didn’t have to pick up our checked bags) and after some lunch and naps, we returned to the airport with ease. The rest of our time pre-flight was spent at the LAX Admirals Club. It’s important to call out that the Terminal 4 Admirals Club (the bigger one) has a kids’ room, which is preferable. The Terminal 5 Admirals Club (see this link for a detailed review and pictures) does NOT have a kids’ room, which means as parents, you’ll need to be more vigilant with containing two rambunctious kids.

::exhausted sigh::

The fact that getting to LA means we were only half done with our flying meant we had to save up our energy – and that nap was key to doing so. Each of the kids crashed for part of the flight and the very sympathetic flight attendant made sure these two parents were well..um, hydrated.

We arrived at Lihue Airport, got our rental car, and headed straight for the Koloa Landing Resort at Poipu, (a part of the Autograph Collection). Arriving at the semi-open-air lobby, one is greeted by beautiful natural wood tones, nice bright lighting, and a warm staff greeting. We were ready to get checked in to our beautiful room when the agent informed me that we had been upgraded to a two-bedroom villa.

UP. GRADED.

Say it with me…it never gets old.

She also handed me a welcome lei, which put me in an even better mood, and informed me that I got market credit each day – so I grabbed a sandwich and some juice to cure the late-night hunger. We got back into the car and drove to building 6, villa 202 – just take a look at this video and be as impressed as us:

We settled into our villa, bemused by the good fortune we received and the welcome spirit we have come to greatly appreciate about trips to Hawaii, and proceeded to get some rest from the journey.

Day 1 (August 26, 2022)

All of that to just get TO Kauai. Now the vacation can start.

This video is both one of the kids babbling and also the nearby roosters waking us from our slumber.

We descended from our building down to the Holoholo Grill, the in-house restaurant at Koloa Landing where we would have several meals over the coming days. Now something you may not know about me is that my great-grandfather was born in Hawaii, my mother spent time growing up in Hawaii, and as a kid, we used to visit every summer (until travel for my paraplegic mother became difficult). As a result, there are several Hawaiian dishes that ALWAYS inspire joy in me. One of them is loco moco – a scoop of white rice covered with a hamburger patty, fried egg, and gravy – usually served with mac salad (not in this case). So naturally that was what I would have for breakfast, and it was delicious.

My kids had been running Moana for at least 20% of the movies playing at home, so when Heihei visited us at the table, both kids were naturally excited.

As we finished our meal, I also noticed a couple at another table – and the woman seemed familiar. After a couple minutes of awkwardly looking over, I realized it was my former Deloitte colleague Christine whom I hadn’t seen in many years. It turns her she and her husband were on their last day in the hotel before heading up to Princeville so she gave me some recommendations before they headed out – what a small world!

After breakfast, we spent the rest of the morning (and lunchtime) poolside, enjoying a complete lack of responsibility or awareness of the outside world.

That evening, we headed to Hanapepe Art Night – a delightful set up of merchants and vendors in the charming town of Hanapepe. Our first stop was Midnight Bear Breads and the smell of their delightful pastries and bread could be smelled a block away. There were a lot of artists selling their wares and while we didn’t buy anything, the whole event was super charming. We also picked up kettle corn from Sumiko’s and some light dinner from the Japanese Grandma cart before packing up and heading to the grocery store before going back to the hotel.

Day 2 (August 27, 2022)

Day 2 took us back to the Holoholo Grill for breakfast – on order today, Kalua pork and Taro french toast. So so so goooooood.

Our first outing took us to Poipu Beach Park where the kids got to enjoy the calm waters and some honu’s (turtles) as well! Even with the naturalists and people warning folks to not get too close, there were still some tourists who got super close to them and got a good talking to.

Lunch was spent at Chalupas and Big Monster Sushi Food Truck, both of which sit in a little parking lot with lots of parking available nearby. I won’t pretend that the Mexican food in Hawaii is anything comparable to that in California or Texas, but it did the job.

For our evening plans, we returned to Hanapepe as we had a reservation at Japanese Grandma’s for dinner – but since we arrived early we decided to go check out the Hanapepe Swinging Bridge beforehand. I admit to a slight fear of heights and this bridge made me a little nervous, but it still provided some incredible views of the water and the lush green banks of both sides.

Dinner was a pretty epic affair. We were seated in an outdoor area behind the restaurant which was both nice and tough as Cooper loves playing with rocks. The food itself was excellent and you can’t go wrong with any of the fresh catch. Clementine befriended the musical performer, who was ably talented in multiple instruments, and also a teacher at the local school. As the sun set on another beautiful Hawaiian day, we returned to the hotel full and satisfied.

Day 3 (August 28, 2022)

After a light breakfast in the room, we set off for the western end of the island and specifically to Waimea Canyon State Park. I didn’t realize this was considered “the Grand Canyon of the Pacific,” and as you proceed further into it, you understand why. Simply breathtaking views (assuming the fog and clouds clear) – and even if they don’t, it’s still marvelous. What follows are each of the lookouts you can stop at.

• Waimea Canyon Lookout
  • Your first stop as you venture into the park will yield multicolored hues of brown and green and gasps of “ooo”‘ and “aaah.” There’s a decent-sized parking lot here – pay for your parking and place the ticket on your dash before going to the lookout itself. Also consider using the restrooms here.

• Waipo’o Falls Lookout
  • More oo’s and aah’s
• Pu’u Hinahina Lookout
  • More oo’s and aah’s
• Kalalau Lookout
  • Okay, THIS is the stunner. I’m not ruining any surprises. Any Google search or even the link here will reveal that it’s “one of the most-photographed and well-recognized valleys in all of Hawaii.” And for good reason.

• Pu’u O Kila Lookout
  • Oh wait, you thought it couldn’t keep going and get better? BOOM.

As we began our return journey, we stumbled upon Kokee Lodge and decided this was a great place to stop for lunch. We had a surprisingly good BBQ sandwich, BLT, and a bowl of soup, and then we were able to get the kids some much-needed outdoor playtime. There’s a massive open field in which they can run, so if you bring your kids here, let them run free! It was also interesting listening to the languages people around us were speaking. We definitely passed a family speaking in Portuguese!

We continued our descent and came upon both a red dirt waterfall and the Niihau Lookout (you can barely see the island) but both were good spots to get out of the car and stretch one’s legs, if only for a few minutes.

After we got back to the hotel, I headed to the fitness center for a light afternoon run, we got takeout dinner from Holoholo Grill, and we proceeded to be amused by a Japanese TV program featuring both Japanese and non-Japanese folks alike speaking about tasty ice cream.

Day 4 (August 29, 2022)

Another day, another round of swimming – this time at the family lagoon. Koloa Landing has its main swimming area, and then it has this lovely secluded section away from the core of the hotel. The pool had maybe five people in it, which allowed us free reign of the area – and the shallow depths made it very safe for the little ones.

Lunchtime today called for Koloa Fish Market – a place I’d heard much about and that we tried going to a couple days earlier (but the line was insane). We parked and got into a decently long line but got to the front in less than five minutes. We ordered and took the food back to the hotel as it was a short drive and within 15 minutes we were enjoying some of the finest poke I’ve ever had. The tuna, for example, is almost gelatinous. And I don’t mean that as a bad thing. It’s soft and chewy and yet it dissipates in your mouth very quickly. The lomi lomi salmon provides a moist, juicy contrast to the rice and kalua pig – and you know a good mac salad or spam musubi when you have it.

Our afternoon away from the hotel took us to the Kauai Coffee plantation, which I hoped would have a little more story or flare to it. Instead, it was really a big storefront with a lot of coffee samples, a nice terrace to enjoy an iced beverage, and then a large self-guided walking area to explore the plantation on your own (which we did).

The return journey took us past The Right Slice, and we had to stop to get a couple pies since we’d passed by this place a few times by now. The pot pie was easy to heat up and super rich and the cheesecake we got was decadent and delicious.

Cooper got to swim til late after dinner, and once he and Caitlin returned, we all went to bed.

Day 5 (August 30, 2022)

Day 5 arrived and we decided to explore the east side of the island. I had planned for us to go to VIP Treats and Sweets and to my sadness, it was closed. I mean I get that you deiced to surprise your daughter and I love that – but I really wanted a malasada. 😦

But as they say, when one door closes, another one opens – and we drove to nearby Haole Girl Island Sweets. I am so glad we ended up here, as we have five epic pastries: the pear/fig/almond franchipan, the ube with coconut, char siu, lilikoi passionfruit curd with cream cheese filling, and the taro coconut muffin. You also cannot go wrong here.

Once we loaded up on baked goods, we drove to Lydgate Beach Park and staked out a little area under some trees for shade. We spent quite a while here swimming, and before we knew it, it was past 1 PM and we were getting hungry again. I asked Caitlin if we could go to Hamura Saimin, a well-known old-school restaurant that is as old as it looks – and that’s a compliment. That means it’s been around forever (since 1906, and in its current location since 1952) and continues to satisfy both locals and tourists alike. We got a monstrous bao, some won ton soup, and saimin (of course) and it restored our energy.

Our last stop of the day was the Kauai Plantation Railway where we discovered that Cooper really loves trains. This place is a bit of a tourist trap, but it’s also a charming excursion from the beach, a chance to play with some animals (and by play, I mean feed them a little), and then the trade winds breeze through your hair. $57 for four of us wasn’t cheap but it was a charming ride and you get to feed the animals too!

We returned to the hotel, getting in one last round of swimming before dinner, and wolfing down flatbread and burgers, along with the pie slices from The Right Slice.

Day 6 (August 31, 2022)

Oh no! It’s our last day in Poipu and we won’t have all of the creature comforts of a hotel! Woe is us!

I mean, you can play at least one short song on that tiny violin for us…

We got in another round of swimming at the hotel pool before cleaning up, packing up the car, and taking off for Princeville. But before we did that, I took the car and drove west to Aloha Sweet Delights (or Delites, depending on who’s asking) to get the only malasadas I would have on this trip (spoiler: they weren’t bad!) and then to Wong’s Chinese Restaurant (in Hanapepe) to pick up some proper plate lunches before our drive up to Princeville.

The path around the eastern side of Kauai takes you through a bunch of cute towns like Wailua, Kapa’a, and Anahola, along the Kuhio Highway. After a little over an hour (maybe longer if you stop), we arrived at our VRBO at the Cliffs at Princeville.

The community feels like it’s a retirement community and our later journey to the pool confirmed that, but the setting was super relaxed. We had one gripe with our VRBO in that it was clearly outdated and in need of maintenance. We plugged a power strip into the wall and it blew the breakers (the owner also never responded when we expressed concern).

But the one thing this place had was a stunning sunset view – the natural light is second to none and all of the residents/guests came out to see what is, I’m sure, a regular occurrence.

Day 7 (September 1, 2022)

Before we get into what we did this day, know something about visiting Ha’ena State Park. It is beautiful, well worth it, and also requires some planning. Let’s begin with some key lessons to prepare for BEFORE you arrive.

• Understand that there’s the official Ha’ena State Park website and then there’s GoHaena.com.
  • Two different websites, but both have critical information you need to know before and the latter is where you make your reservations for tickets.
• Buy your ticket for whatever date and time you can get.
  • This window opens up 30 days in advance.
• Determine what you’re going to do before you get there.
  • We only visited Ke’e Beach. But you can actually hike part of the Kalalau Trail. If you have little kids, you probably won’t hike the trail. But google the photos and determine for yourself!
  • Understand how the shuttles work: https://gohaena.com/shuttle-schedule-stops/
• When you get there.
  • Park your car where the attendant tells you
  • Screenshot or take a photo of your hop-on pass codes
  • Get back on the shuttle: get your name on the list as soon as Sherman (or whoever is working there) shows up

We had our snacks and drinks prepared. We had the backpack carrier for Cooper, the Lille for Clementine, and backup activities (like the Kindle Fire) in case they didn’t want to play at the beach. We drove down to the parking area where you’re supposed to park and confirmed the timing of the shuttle. This is where you should have screenshotted or photographed your pass.

When the shuttle takes you into the park, it will drop you at a sheltered area with picnic tables where you will come back to pick up the shuttle bus. We packed up the kids and walked out to Ke’e Beach where we set up camp about 20 minutes after we arrived.

The beach is tranquil, the waves light, and there’s plenty of shade.

There are also a ton of birds looking to scavenge your food, so keep things closed or sealed when leaving your camp behind.

We got back to the shuttle drop-off point around 1 PM hoping to catch that shuttle back. Therein proceeded to be one of the longest delays I’ve ever found with ground transportation. The bus did not arrive until 2 PM (apparently there was a traffic jam) and both kids were a little restless having waited patiently for nearly an hour. I gotta say I was super relieved to board that bus.

We got back to our car around 2:30 PM and decided the way to get over that long frustrating wait was to get some lunch at The Hanalei Gourmet, which consisted of a tasty Reuben and a bunch of fried foods for the kids. Something to note is that you may pass the Hanalei Valley Lookout and if you do, I encourage you to stop. If you do, you’ll have moments where you feel you’re in Vietnam or another Southeast Asian country, where the splendid paddies and fields in the shadow of the mountains will awe and inspire.

As the afternoon/evening wore on, Caitlin and Cooper played on the condo playground while Clementine and I watched movies.

Day 8 (September 2, 2022)

“Sheesh, you folks were there for 8 days? Didn’t you do anything else besides beaches?” some of you might be thinking.

I mean, have you been reading or watching my amusing videos and seeing my cute children smile for the camera?

We attempted to go to the Kilauea Lighthouse but apparently, we needed reservations – reservations we did not have. So we made a game-time decision to head to nearby Anini Beach, and this was another huge win for us. It was the most secluded beach we went to the entire time we were on Kauai but there’s not a lot of parking so I recommend going early.

After the beach, we drove to Hanalei Pier, which just so happened to have the Pat’s Taqueria food truck in its parking lot. We grabbed burritos (which were good compared to the previous Mexican food truck) and then wandered to the end of the pier. If you do this and turn back, you will see why this place is legendary.

To reward the kids for good behavior, we went to Pink’s Creamery (the Mango and Cream was outstanding) and stopped by Big Save Market in Hanalei for some groceries before we headed back to Princeville.

As we prepared dinner, a little bird landed on our lanai – talk about one cool hairdo!

Day 9 (September 3, 2022)

Back on day one, my ex-colleague Christine (whom we ran into at Koloa Landing) told me about Holey Grail Donuts and insisted we try it. So knowing we had to drive to Lihue airport, I got up early and drove down into Hanalei to pick up these supposedly epic donuts. And oh my lord…they were the best donuts of my life.

They’re made with taro and fried in coconut oil, which gives them a wildly different flavor or texture than any other donuts I’ve ever had.

At that moment, I started writing descriptions so I could remember these four flavors that were available that day:

• Saffron Snickerdoodle (top left): Of the four, this one sounded the least interesting. And let me be clear, ALL of their donuts are delicious. This brings back memories of your typical cinnamon sugar donut in terms of texture, but that taro cake center is dop.
• Shamma Farms (top right) – I had to look up what calamansi is. It’s a kumquat-citrus hybrid fruit grown primarily in Asia and known colloquially as the Philippine Lime. It adds such a wonderful touch to this donut. I’d take a dozen of these.
• Chocolate Crunch (bottom right): I mean, really how can you mess up a chocolate donut? The answer – you cannot. Certainly not here.
• Miso Honey (bottom left) – This is what I wrote the moment after I took the first bite: “it tastes like what God‘s version of French toast with a sprinkling of black sea salt might taste like.” That’s it. If they’re serving this one, get it. NOW.

Each is lightly crunchy on the outside but only enough to give you a small crunch. Then you get to the soft, chewy interior. It’s not spongy like most donuts – and maybe that chewiness comes from its Taro roots… pun intended. Hahaha. I added on a draft coffee (heads up – all their drinks are iced) and it was magical.

I grabbed a hot coffee from Foodland for the wife and raced back to the VRBO so we could finish packing. We then loaded our car and drove back to Lihue where we gassed up at Costco (it was the cheapest gas by almost a dollar a gallon), dropped the luggage at the airport, then returned our rental car to National. We had a quick bite to eat at the airport before boarding our flight to Los Angeles.

Our return flight to LA came with an overnight layover and we decided to stay at the Four Points by Sheraton Los Angeles International Airport. Let me be clear: DO NOT STAY HERE.

There are better hotels, but also their shuttle did not pick us up despite multiple calls to the hotel (which did not yield any action). Only because we were lucky and another hotel shuttle driver took pity on us did we get to our hotel (with all our luggage and car seats, cause we had to take it out of the airport). We thankfully gave that guy $20 but we shouldn’t have had to. And the next morning there was no breakfast, the coffee shop was closed, and we were snarling, caffeine-less parents.

Day 10 (September 4, 2022)

The next morning, we returned to LAX with no issues, checked in for our flight, and we were home that evening.

Final Thoughts

(this first part was written on September 3, 2022)

If your gas tank is running on empty, Hawaii has a magical way of refilling that. Whether it’s the combination of sunshine, swimming, and salt water, beautiful lush greenery everywhere, or maybe just the fantastic food – you leave here full. Your skin shows it. Your belly shows it. Your heart shows it.

Here I am nearly nine days after arriving and I’ve adjusted to the time zones, begun to acclimate to the humidity, and long for that salt air cross breeze that zips through our VRBO.

(this part was written on September 6, 2022)

Okay, that was two days ago. 

It’s 1:22 AM on Tuesday, September 6. I’m writing this particular paragraph because my time zones are completely fucked up. It’s the equivalent of 8:22 PM and the reason why I’m still awake is because I needed to write, I couldn’t sleep, and just even thinking about the places we went, the sights we saw, and the food we ate brings me to life.

Holding Anthony Bourdain’s last book (appropriately titled “World Travel”) reminds me of the satisfaction that both travel and reading bring me. Nothing replaces a heavy hardcover book and even though it’s not efficient like my Kindle, it leaves a stronger impression of the words than digital ever could. It’s thick and I feel the weight of the books on my fingers as I try to read it while lying on my back.

(Last part written July 3, 2023)

Part of me is embarrassed it has taken me nearly a year to write this trip up. But finding free time to write is incredibly challenging with two kids under four, a day job, a side job, a nonprofit board role, and the rest of life’s inevitable distractions.

That said, I am also incredibly grateful for what our trip to Kauai gave us. A restful time for us to get our Vitamin D, some sleep, lots of exercise, and some great food. And now I have a new favorite Hawaiian Island for us to visit in future. Thanks Kauai. 🙂

ooh. last thing. Here are some key lessons I learned that you should keep in mind as you plan your trip!

Some important callouts to do BEFORE you leave

Activities

• Plan your lodgings and time in each part of the island accordingly.
  • We did six days on South Shore, staying in Poipu and visiting Waimea Canyon and Hanapepe. We then moved up to the coast to Princeville for three days but I think we could have used one more day on the North Shore.
• Book your Nā Pali Coast Boat Tour in advance and anchor your trip around it!
  • We did not get to do this because of a confluence of factors. Most tour operators do not permit children below 4 or 3 years old (varies by provider) – we learned that the hard way. And there wasn’t the availability we wanted because we tried to book while we were there.
  • Boats depart from Port Allen (South Shore) or Hanalei (North Shore) so I would choose the departure based on where you’ll be staying and for whichever dates you’re there.
  • We did not try to take a helicopter tour but the same principle applies – check to see if your kids are eligible and which provider has openings for the days you’re going to be on the island).
• Book your visit to the Kilauea Lighthouse (North Shore) in advance!
• Book your visit to Ha’ena State Park — I would recommend using GoHaena.com for ease of experience – do this 30 DAYS IN ADVANCE of the date you want to go to Ha’ena (which is on the north shore). Read below to Day 7 for our experience at Ha’ena and Ke’e Beach.

Packing

• If you bring a water bottle or reusable coffee mug, ensure they fit in your car cup holder. I use this amazing coffee mug from Swagger (see the first image on their page) but the bottom is wider, and hence doesn’t fit in a standard cup holder.
• If you don’t want your baseball cap or favorite sunglasses getting wet, bring a set of both that are specifically for the pool. I especially like a trucker hat for the pool along with a pair of Shady Ray’s – if you use my link, you’ll get $20 off your first order, and you can replace a pair for $10 WHEN you lose/break it – I stepped on my pair on the second to last day of the trip.
• If you’re traveling with infants, bring a bottle brush to be able to wash baby bottles out. Most places will include a sponge but it’s not as easy to use on tiny bottles.
• We brought a bunch of suntan lotion (because it’s way more expensive in Hawaii than on the mainland) but did not bring aloe vera – if you’re prone to burning, bring some aloe vera! Also don’t forget any lotion like Cerave or Aveeno if you have dry skin/eczema. Going in and out of the water and sweating all day can exacerbate your conditions!
• Bring Ziploc slider storage bags (Costco) or Stasher silicone bags (we got ours on Amazon) and use them for resealing snack bags, bringing sandwiches to the beach, and ensuring gifts (like sauces) or bottles of suntan lotion/shampoo don’t leak everywhere!
• You NEED two pairs of shoes: walking shoes (ideally slip on’s) and sandals. I bought these Olukai slip-on sneakers and these Olukai sandals (with their fabulous arch support) specifically for this trip. If you plan on going running, bring a pair of running shoes. If you plan on going hiking (anything off-road, trail, over two miles) then bring a pair of hiking boots. This is all you need.

Some important callouts to do as soon as you arrive

• Buy a water jug. Once you are in a hotel, VRBO/Airbnb, or a private home, you will be thirsty a lot and we want to have water readily available.
• Whatever you didn’t bring, go and buy it ASAP. Have it for the trip. For us, that included peanut butter and jelly plus bread for kids’ sandwiches, beers, juices, bacon for Cooper’s breakfast, fruit, and any chips or snacks needed for the trip. It’s way easier to have things before you get settled in at a hotel or VRBO.