A 50th birthday is a pretty big milestone. And mine was coming up.

I usually don’t feel like my birthday is a big deal, but turning 50 is different. It’s the big transition from the youthful decades to the second half of life (though nobody expects to live to 100).

Despite that milestone, as a family we’ve also gone through a lot of ups and downs over the past couple years. Every few weeks a new challenge would emerge and so would the stress. It felt like a gauntlet and I longed to return to the simpler days of the past.

So with that in mind, it was hard at first to consider doing too much for my 50th. A roadtrip perhaps. Or maybe nothing at all but a few days of rest at home.

But early in 2025 I began to think about it more. I longed to go someone warm. Beaches, tropical weather. I thought about Belize, a place I went in 2002 when I was 26 and enjoyed as an adventure. I thought of the Yucatan in Mexico, and places father afield. It couldn’t be too complicated or be a place we were likely to visit on a subsequent trip in the next couple years. And it had to be a place that would be relaxing and fun.

And then I made up my mind. It was time to go back to Kauai.

My wife and I went when we were still dating in 2003. We were young and still figuring things out. We were adventurous and care free. We saw and did a lot on Kauai with a couple additional days on the Big Island. But we left a lot unseen and undone, never expecting that by 2025 we would still not have returned.

I viewed it as an opportunity for all of us to take one last family vacation. My eldest Daniel is 19 and in college. His only visit to Hawaii came in 2007 on a trip to Maui (our last visit to Hawaii). He was 11 months old at the time and had no memory of the experience.

My youngest had never been to Hawaii at all.

We were now a family of two aging parents and kids growing into adults, and I felt like we could all go to Hawaii as a family. The kids would get to experience it for the first time and we’d get to go back to a place we last experienced as two unsure about the direction of life twenty-somethings.

After we made our initial plans to go just to Kauai, we began to think a little more about extending our trip to include Oahu. Our flight back already had a connection in Oahu and only I had ever been to Oahu, when I was 13. The family wanted to visit Pearl Harbor and my wife and I found a number of additional things that we wanted to do in Oahu as well, including a UTV ride.

After some planning that removed any moments of relation from the trip, we had built out a fun eight day adventure for Hawaii. Evan would miss a couple days of school and my eldest would miss some class time, but we’d hit all the major stuff that we really wanted to see and do without feeling like we had any real regrets about what we didn’t do.

Hawaii is expensive and not a place we can travel to often, so we might as well do as much as we can within those eight days.

Day 1: Flight to Kauai

We are lucky to live near a major city with a major hub airport. We have a lot of direct flights that a lot of other places don’t. Denver International is a massive airport and not a relaxing experience, but it does offer a lot of direct flights.

We had a direct flight to Lihue leaving at noon. Easy. No getting up really early in the morning. No ending the work day and frantically packing everyone up and rushing to the airport.

We were all seated together in extra legroom seats and our seat backs had entertainment screens. The flight was an extra hour long though and for whatever reason United Airlines seems to have cut back on the beverage service. My wife and I might have ordered a mai tai, but instead they offered only a tiny cup of soda after seven hours in the air and never came by at any time between the lunch service at the beginning of the flight. Their loss.

Lihue, Kauai

Once we arrived we were met by the warm, humid air of Hawaii and all of the lush green foliage. And the hot sun. And a blue ocean in the distance just outside. That’s what we came for.

The tiny airport took only minutes to exit, but we had to rush onto the shuttle for the rental cars as a horde of people who arrived after us made it clear they were not willing to wait their turn.

Once we got our rental car we stuffed it with our luggage (we were honestly overpacked), and started on the ultra slow road to Poipu.

It was at this point that my eldest got cantankerous and irritable. For whatever reason he decided to pick a fight with my youngest in the back seat over nothing and I eventually lost my temper as well. This is my birthday trip. Shut up and get along.

After an hour of slowly proceeding through rush hour traffic in a place with only 60,000 or so people, we got through it and drove the rest of the way to Poipu.

Poipu

Early on in my planning I had decided that I wanted to split our time on Kauai between and south and north shore. I decided upon Poipu because of the popular beach which I wanted to be able to easily visit without a drive.

We found the Castle Kiahuna Plantation where we had reserved our VRBO and lugged our stuff inside. Once sort of settled, Shelley and Evan went to pick up a Walmart order back in Lihue (fortunately the traffic was clear on the return trip) while Daniel and I unpacked and tried to figure out a plan for dinner.

Daniel pulled out his laptop to work on a school project (still seemingly annoyed by the earlier argument and acting as though he regretted coming) so I stepped outside to find the beach. It was right outside at the edge of the condo complex. It was sunset and I took my first photo of the trip from Kauai.

I walked back into the townhome and decided that with darkness setting in we would be best off just getting Kenji Burger to go from Lihue, where Shelley and Evan were getting the Walmart order. When I relayed that info to Shelley she was unhappy, as she wanted something ore after a long flight. I just couldn’t find very much nearby and with it being dark I didn’t have a good sense of what was good (and not outrageously expensive).

They returned with all of our groceries for the next several days (which would save us time and money on many breakfasts) and the Kenji burgers. Once everyone was fed and able to relax the mood improved. Still, I wasn’t feeling that great after the grumbling and decided that it was best to just call it a night. We were, after all, four hours ahead of the local time zone and had no time to adjust.

Day 2: Poipu and Waimea Canyon

I struggled to sleep past 3AM. Eventually at 4AM I gave up.

I wanted to get outside and explore and despite it being dark, I did just that. Outside a cat greeted me, and then I almost stepped on a huge frog.

I wanted to find the path from the condos to Poipu Beach (which isn’t a straight walk on the shoreline due to the terrain), and found the passage in the darkness. It led to a cement walkway past a hotel and to the surf and sand.

I trudged onto the sand with my phone flashlight on and two little kids ran past in the dark on the beach. That was strange, but I guess it’s safe. I walked onward and found the crescent arc of Poipu Beach Park, but no turtles were visible to me (I was on the wrong end and couldn’t see them in the darkness). Still I had at least found the beach access way.

Returning to the townhome I found Shelley was awake and was eager to go visit the beach at sunrise. I told her about the passageway to Poipu Beach and we went together back to where I had been only moments before. This time we found the turtles.

We enjoyed watching the turtles slowly inch their way back into the surf. I had been hoping to see the turtles which frequent Poipu Beach and we had found them early the first full day of our trip.

We stopped off for coffee and bought some Hawaiian bread across the street from the park, then walked back to the townhome where Daniel and Evan were still sleeping. Along the way we found this enormous snail on the pathway.

Reentering the townhouse, we found Evan wake and told him about our discoveries. He was eager to see them too so I took him to Poipu Beach (my third trip that morning).

We not only saw the sanil and the turtles but we found a couple sea cucumbers stranded on the shoreline. Evan and I gently push them back to the surf where they hopefully survived. We were proud of ourselves for rescuing the sea cucumbers.

After returning again to the townhouse, we fund everyone awake and I finally got a chance to eat some breakfast. I stepped onto the patio where we could enjoy the surrounding tropical foliage, numerous birds, and the horde of beggar chickens.

The last time we were in Kauai there were a ton of feral chickens running around. In the twenty-two years since, that number has now seemingly increased. They are literally everywhere you go.

If you are not familiar with the story behind the chickens it dates back to 1992 and Hurricane Iniki. Apparently there were a lot of Asian workers living on the islands that raised a certain breed of fighting chickens. When the storm hit, the chickens were set free and thrived on the island.

Because they are fighting chickens the meat is tough and so no one catches them for food. They have no natural predators on the island. The chickens have become a part of Kauai’s identity and now show up on souvenirs like shirts and coffee mugs.

Once everyone had eaten breakfast we strated off for Waimea Canyon.

Waimea Canyon

Kauai is full of scenic wonders that are pretty much unmatched in the Pacific region. Among these sites is Waimea Canyon.

The drive up to Waimea Canyon is a pretty steep ascent from the coastline town of Waimea. Once at the top the first viewpoints off that breathtaking vista that makes it worthwhile.

Waimea Canyon is called the Grand Canyon of the Pacific, and though it isn’t quite that deep, it’s still dramatic. We pulled off at a couple viewpoints, before finding that the main viewpoint area was closed. We proceeded on to the Pu’u’hinahina Lookout which wasn’t quite as impressive as the previous roadside viewpoints, but i did provide access to the trails.

Waimea Canyon Trail

It’s pretty rare that I take a hike and bring back no photos from the experience. But the Waimea Canyon Trail was one of those times.

The issue here was dense folliage and thick, sloppy mud. I couldn’t pull my camera or phone out for risk of getting it covered in mud. The first half mile down was reasonably passable, but after that the trail was a quagmire of wet mud.

Daniel and I traveled a full mile into it before we gave up. I was wearing old running shoes that provided almost no traction. After descending a couple hundred feet we had to go up a slope and I was sliding and slipping and holding onto branches and vines trying to stay upright. His hiking boots fared better but he was still covered in mud.

We hiked back up the trail, advising anyone without the proper shoes or clothing to not go much farther. Once back at the parking lot all four of us used a water spigot to try to clean ourselves up. My shoes were totaled and I pretty much decided that I would throw them away before the trip came to an end.

Kokee State Park

Since hiking wasn’t going to happen we continued on to Kokee Stat Park. Kokee State Park offers a view of the Na Pali Coast called the Kalalau Overlook. We parked and walked up to the overlook, our feet still wet from dousing them at the Canyon trailhead.

We also saw some of the light blue hydrangeas we had seen growing there in 2003. A our wedding a year later we had blue hydrangeas for decorative flowers.

Tired and hungry we decided to drive back down to find lunch. First we would stop in Waimea at a Big Save Mart, which a local woman at Waimea Canyon recommended for cheap flip flops (since we really couldn’t wear our shoes into any restaurant).

In Waimea we found the Big Save Mart and bought some flip flops, cleansing wipes, a couple cheap snorkel masks for the beach, and some pre-mixed mai tail and run punch cocktails to enjoy later that night at the townhouse.

After getting cleaned up be headed off to Koloa to enjoy a good sit down lunch.

Kauai Island Brewing Company

One of the things I love about Kauai is how rustic many of the towns are. Koloa is a great example of that. It’s a small, historic town on an island that feels like it could be in foreign country. There are no tall buildings on Kauai and everything in the rest of the world feels far away.

Our first impression of Kauai Island Brewing wasn’t all that great. We deicided to sit inside and were seated at a table in a busy passageway. But soon another family left and we asked if we could move into their more relaxed booth seat.

I don’t know why I didn’t take any photos of the food, but the appetizers were really standouts. We ordered calamari and poke. The calamari was huge (something we mainlanders can’t comprehend is possible) and the poke was so good I thought about ordering an appetizer for my entree.

I ordered a entree and honestly don’t remember what it was. I should have just ordered more poke and calamari. The beers were great too and much needed.

Poipu Beach

After returning to the the condo we changed into our swimming trunks and grabbed our snorkel gear before walking back to Poipu Beach (my fourth visit of the day). This time though I was going to get into the water.

While the sandy beach is great for lounging and turtle viewing and the water is warm, the undersea surface is a rocky, old coral surface. We didn’t bring water shoes and our feet got cut several times as we swam in the shallow bay.

As the short video shows, there were plenty of fish to be seen, but we just weren’t ready with water shoes for the shallow.

Despite the cuts and scrapes, we took the snorkel gear back to the townhouse and went to the beach nearer to the complex: Kiahuna Beach. The beach was sandier here and easier to swim in, but there were still some rocky spots which hurt our feet. Nevertheless, we swamp for aout an hour in the surf.

I didn’t have any cameras with me which was unfortunate because a harbor seal swam right by us as we stood in the surf. It was pretty cool.

Puka Dog

To close out the day we walked over to Puka Dog to try out the incredibly popular hot dog spot in Poipu. We enjoyed them on the walk back to the townhouse where Shelley and I also poured ourselves some cocktails and relaxed on the porch.

After that, we had a big day ahead tomorrow and needed to get to bed to rested and ready.