Hawaii, August 2026

 

Why Hawaii?

I mean I guess you could say "why not Hawaii" (always), but in planning a family trip to celebrate my 50th birthday (which isn't actually until November, but we are beholden to the school calendar so we went in August), Hawaii was where I wanted to go.  Initially I had planned to go to the big island as I’ve never been there, but then I decided I really wanted to go back to Maui; Jourdan and I had been once before -- in October 2009 -- when I was 8 weeks pregnant with Russell, so now seemed like a good time. This trip was also my second really big travel points redemption (the first was when we went to Orlando and stayed in a 2 room suite at Universal Studios in 2024), and I was so excited to be able to book us two adjoining rooms at the Hyatt Regency hotel "for free" (on points)!

Sunday, August 9
Travel day!  We were on a 6 a.m. flight out of Billings, so we were up bright and early, but everything went smoothly, and we were checked into the hotel around 1 p.m. Hawaii time (just over 12 hours after we left our house).  Everyone wanted to go to the beach, so we stopped at one of the restaurants at our hotel (where I had AMAZING street tacos made with “fresh catch” fish) and then headed to the beach just off the hotel.  The kids played for a couple of hours (and accumulated probably half the sand from the beach on their bodies), then we headed back to our rooms to shower.  My friend Katy had gifted me a club access pass for the hotel so we went to check out the evening appetizers at the club, then walked around the resort a bit.  Fun fact: there are penguins that live in the lobby of our hotel so we set out to find them as we hadn’t seen them yet.  We then went back to the club for dessert, then up to the room.  We were in bed by 8 — midnight Montana time — which did not feel too early for the long day!

Jourdan ended up in a row all by himself on the flight from Seattle to Maui!  He called it "first class the cheap way" 

Picture of how Russell got so much sand on his person 

Hotel lobby fun, including penguins! (The Aloha pictures were taken on different days)

More fun around the hotel (the swan picture is one Jourdan took on an early morning run)

Monday August 10
I had arranged for family pictures and purchased matching Hawaiian floral attire for us (from Hilo Hattie’s — I wanted to buy something made in Hawaii) so we got up and got matching and met the photographer at Ironwoods Beach at 7 am.  Side note: Jourdan thought we looked ridiculous matching.  I thought we looked adorable.  I was obviously the one who was correct!

Sneak peak of the pictures -- I'm saving them for our holiday card but here is a tease 😀

The top photo is a selfie we took in the hotel parking lot.

After pictures, we went back to the hotel for breakfast in the club then to rest for a bit before heading up to Haleakala.  Our keys wouldn’t let us out of the self parking lot when we tried to leave and there was maybe a moment when we worried our rental car would have to live at our hotel forever, but someone finally was able to come and help us.

We drove to almost the summit of Haleakala; we had planned to do two short hikes, but were running later than anticipated thanks to the parking lot issues, so just did the first part of Keoneheehee Trail (also known as Sliding Sands Trail for reasons that soon became apparent).  It starts at 9730 feet and descends; it can be as long as 11 miles, but we just did the first mile down and then back up.  The down part felt deceptively flat, and I didn't really realize it was a hill until we were on our way back up!  Walking over the sand and looking into the crater, it felt like we were on Mars, or the moon, or some other place that was not earth.  It was windy and a little chilly that high up and some of us claimed that they were not reminded to bring a jacket (which they were), so there may have been some tears initially.  But dad's rain jacket came to the rescue and in the end we survived.  My hip didn't love the uphill on the sliding sand (and I'd forgotten my hiking poles), but other than that it was really an amazing hike.

On the way down Haleakala, Jourdan decided to recreate the first time we had gone — we went early in the morning to watch the sunrise and ran out of gas in a the visitor center parking lot as we were leaving, and had to coast down the mountain.  So he put the car in neutral and down we went.  We made it — but much lower stakes this time since we actually did have gas in the tank.

From Haleakala, we went to Mama's Fish House for a late lunch/early dinner.  I had made reservations back in March, and 3:00 was the latest time they had, so we took it.  There is a reason this is such a famous restaurant; both the view from it, and the food.  When making the reservation, they asked if it was a special occasion so I had said it was my birthday (because technically that was the reason for the trip, even if it wasn't REALLY my birthday), so they sat us right next to the window to see the beach, and there was a card on the table wishing me a happy 50th birthday.  The food was INCREDIBLE.  I think Russell maybe won dinner with a macadamia nut crusted Kanpachi stuffed with crab and lobster, although Jourdan thought his ahi, mahi-mahi and uku curry was just as good if not better (i didn't try it because it was spicy).  I had an uku dish that was also fantastic.

After we were stuffed, we went to the beach off the restaurant where there were giant sea turtles resting in the sand.

We went back to the hotel and walked along the beach there a little, then later got a snack at the club before going to the roof of the hotel for Tour of the Stars, a star gazing talk led by an astronomer.  I had done something similar once before at a hotel in Tucson, and it had been SO cool -- they fixed the telescope so you could see the rings around Saturn, and moons of Uranus.  This talk was not quite so good.  It's not their fault that the only planet visible was Venus, and it was only visible for the first 3 minutes we were on the roof, but it was still cool to see different constellations.  And we did get to see Pluto -- which I still think of as a planet even though I know that shipped sailed a long time ago.

Tuesday August 11
This morning we headed out right after breakfast to do the Waihee Ridge Trail hike, a little more than 4 miles total (my watch said 4.4 miles) with a 1604 feet elevation gain.  Because my hip hadn’t done fantastic on the short Haleakala hike, I made sure to remember my hiking poles.  And they really did help, almost like my orthopedic surgeon knows what he’s talking about! 

The hike started with a 0.16 mile paved straight uphill jaunt that had my kids calling me a liar for telling them the hike was “moderate” (in fairness, the guidebook called it "moderate to challenging" but I left out the challenging part when trying to sell it.  But thankfully that was the steepest part!  The rest of the hike was, in fact, challenging but incredible.  We hiked through forest and along ridges and had the most spectacular views of Maui and the ocean.  The top is supposed to have even more amazing views of the island, but when we got there we were deep inside a cloud.  Which was kind of a bummer, but also really cool in it's own right.  It felt like we were in Jurassic Park and I kept looking for an apatosaurus head to pop through.  The hike was muddy and slippery in parts, which would mostly be a nuisance on the way down as everyone except Jourdan fell at least once — I’ll leave it to the imagination which of the kids got the muddiest (if you know my kids you won’t have to imagine hard).

The steepest part of the hike!

They made it to the top!  (Of the first .16 miles)

At this point, about halfway up, only Russell had fallen so far

We just thought this was a cool tree

We thought these trees looked like the folklore album, so we had to take a picture

At the top of the world, in the clouds

An example of the slippery mud we encountered on the way down

We stopped at Ula Ula Cafe for a bite to eat after the hike (cannot recommend — they served us all at different times and we had to end up taking Russell and Jourdan’s food to go because it took so long, and the food was only meh), then headed to the Road to Hana for our zipline reservation.  I had found our place by searching for family ziplining in Maui and we ended up at Jungle Ziplining.  In contrast to lunch, I could not recommend this place more.  Our guides were funny and personable and flying through the air over the jungle was such a cool experience.  Some of us (everyone but me) felt more comfortable letting go of the rope and laying down while flying that others (me).

At lunch, there was someone who would take pictures of you with birds for a donation to a bird sanctuary

We had to cross a (slightly scary) suspension bridge to get between zip lines

This is the one time I let go with one hand -- for like 10 seconds

Jourdan and Owen were more adventurous than the rest of us

Pretty cool to be flying over the jungle!

That evening, Jourdan and I had made an adults-only reservation at Merriman's restaurant (our friends Shannon and Chris had recommended it from their trip to Maui earlier this summer).  It had an amazing location on the water and we got to see the sunset.  We had taro hummus as an appetizer and delicious fish dishes (close if not equal to Mama's Fish House); we made the kids eat the free appetizers at the hotel club for dinner; they were less impressed, but Jourdan and I were ok with that.

Wednesday August 12
This morning we were scheduled to do a clear bottom kayak and snorkeling tour so we were up and out of the hotel at 5:15 to get to the beach by 7.  When we got there, I got a text saying the guides felt the waves were too big, in the setting of a developing tropical storm (more on that later), to safely do the tour so it was canceled.  We were super bummed as we had been really looking forward to it, but obviously appreciate the safety precautions.

Our plan for after kayaking and snorkeling was to rent boogie boards and go play with them at the beach, so we pivoted and did that earlier than expected.  We were on the boards in the water by 8 AM and stayed there until almost noon — we had so much fun!  By the end the waves were HUGE.  When we finally decided we were done, we packed up the car and walked to a craft fair taking place across the street where we bought some souvenirs, then headed back to the hotel to shower.  (SO much sand, even after showering extensively at the beach before we left.). We also discovered just how sunburnt we all were — everyone but Jourdan — despite wearing sunscreen (well at least some of us wore sunscreen; others of us "wanted to get a tan" so elected not to put sunscreen on and paid the price).

Julia really wanted to be buried in sand at least once this vacation

I thought the wind + salt water + humidity gave me a mad scientist vibe with my hair!

We walked down the beach to a restaurant called Monkeypod for dinner (owned by the Merriman's people).  On the way there my (favorite, multi color Keen) flip flop broke!  I bought the flip flops on clearance while on maternity leave after having Owen, who just turned 14, and wore them a ton, so I suppose I got my money’s worth out of them.  But I was super bummed.  Lucky for me, there was a 30ish minute wait for dinner and we walked around the shopping complex where the restaurant was, and there was an Olukai store so I got new flip flops that definitely have a Hawaii flare — a functional souvenir and kind of a necessary one because walking the approximately 0.8 miles back to the hotel on a broken flip flop was not a super appealing thought.

Broken flip flop!  (I am obviously going to try to salvage it with super glue, because I am me)

My cute new sandals

Sunset on the walk back to the hotel, with gelato

Thursday August 13
Today our plan was to hike the Pipiwai Trail which is at the end of The Road to Hana.  This is a trail through bamboo forest and is maybe the thing I was most excited about for the trip.  I had wanted to be up and out the door early, but life (maybe more specifically, life with teens/tweens) happened and we hit the road more than an hour later than planned.  Then our GPS started taking us down a road in the middle of the island rather than The Road to Hana to the start of the hike (which was fine as we planned to do Road to Hana stops on the way home anyway).  About 30 minutes in, we stopped at a fire station because Jourdan has wanted to buy a Maui County Fire Department shirt as a souvenir and to support them after the devastating 2023 fires, and he learned that the road we were on is actually closed closer to the trailhead during weekdays. . . So we had to turn around and drive the 30 minutes back to the road that would take us on the Road to Hana and then start over, and ended up being even later.  The scenery along the road is breathtaking at times (it is famous for a reason), and super twisty and turny.  We arrived at Hana around noon and decided to eat lunch before continuing on to the hike.  We sat down at the restaurant at the Hana-Maui resort, and the tv right above us was playing a Little League World Series game featuring the team from Montana — which is the all star team (ages 10 and 11) from Big Sky Little League, the league in which Owen played all his little league years.  One of Julia’s classmates is on the team and a few kids that had been on Owen’s teams/teams Jourdan coached in the past.  It was super cool to watch them from around the world (and they ended up winning!).

On the drive, we listened to a playlist to which every family member had contributed 10 songs.  One of mine was Living on a Prayer, and while it was playing we passed two road signs that said “slippery when wet” — which is of course the name of the album that contains Living on a Prayer.  It made me incredibly happy.

After lunch we set out for the hike.  There are actually two with the same trailhead — Kuloa Point Trail which is short and takes you to the pools at 'Ohe'o.  These are a tiered series of pools of water that are yet another wonder of nature.  (They are called "seven sacred pools" even though there are more like twenty pools, and apparently the "sacred pools" name was given only in the last 100 years to promote tourism.)  The first time Jourdan and I went to Maui we swam in them which is maybe my favorite memory of that whole trip.  You are no longer allowed to swim in them, but it was still cool to see them.  That hike took about 30 minutes, then we set out for Pipiwai Trail.  The guidebook said it was 4 miles and took 3 hours; my watch said we walked 4.12 miles total between the two hikes (and it took us around 2.5 hours to do both), with about 620 feet elevation gain.

The hike was incredible.  The first mile or so was through forest with giant trees with roots sticking out of the ground, sometimes acting as legit obstacles.  They looked like if they were in a horror movie they would come alive and wrap around us and pull us into the ground.  We got to see Makahiku Falls about half a mile in.  Then about a mile in we got to the bamboo forest — walking through it was so, so cool.  The trees would hit each other and make a clicking sound, it sounded like there were people playing castanets all around us.  And then at the end of the hike was Waimoku Falls — it was gorgeous.  The whole hike was definitely a highlight of the trip.

Pools at 'Ohe'o

Tree roots that thankfully did not (purposefully) threaten our lives

Various cool things on the hike

Bamboo forest

Waimoku Falls

We stopped for a picture at the National Park sign on our way back to the car

It was almost 5 by the time we got back in the car, which meant we didn’t get to do many stops on the drive back up The Road to Hana.  Jourdan had wanted to stop at Twin Falls and do another short hike and then swim under the falls, but we weren’t able to do so.  Instead we drove back to the hotel and got back around 8:30, and went to bed.

Road to Hana sights on the drive back

Friday August 14
Our last day on the island, so we planned to go to the beach one last time.  There was a beach about a mile and a half away from our hotel that has a black rock cliff from which you can jump, and Jourdan really wanted to do that so we walked down there.  Tropical storm Lala was still aways away but sending wind ahead of her and at times there were gusts up to 20-30 miles per hour.  The waves were HUGE and strong.  Jourdan jumped off the cliff (Owen would later too but we don’t have photographic evidence of that), and we all waded out into the water.  After being knocked down by waves multiple times (including at least twice when the waves flipped me head over feet 360+ degrees under water — scary, not fun), I was kind of done with the water.  Russell had a pretty bad sunburn from our first beach day and the wind blowing sand on it was painful so he was also done, and Julia was (understandably) afraid of the waves, so the three of us headed back to the hotel while Jourdan and Owen stayed and played a bit longer.  (That’s when Owen jumped off the cliff.)  If I had thought we out a lot of sand in the shower before, I was wrong because there was so much sand in our suits after all the underwater acrobatics and body slamming into the ocean floor the waves had caused.  Like SO much sand.  Even after rinsing off extensively at a beach shower!

Jourdan cliff jumping

After Jourdan and Owen made it back to the hotel and we had all showered and changed, we drove to see the famous Banyan tree in Lahaina.  The tree was planted in 1873 and is the largest in the United States.  It suffered severe damage in the 2023 fires and is being rehabilitated so was roped off so we couldn’t get close.  We also saw many burned buildings and the temporary housing that had been set up after the fire.  I know that fire behavior is unpredictable, but it was so interesting how there would be a row of completely burned buildings and then across the street the buildings looked fine.  Overall sad.

The Banyan Tree

Next our plan was to go shopping at a local market but we decided we didn’t want to drive quite that far (everything on Maui felt like it was an hour drive), and instead went back to the shopping at the hotel, and got some souvenirs (shirts from the clearance rack — my favorite! — and a Christmas tree ornament as is our tradition).  We had also previously purchased some Maui-made hot sauce, Hawaiian salt, and the kids had gotten some jewelry from the market by the beach on our first beach day.

For dinner we had reservations at Hali’maile General Store, which was a restaurant at which Jourdan and I had eaten on our first trip to Maui.  We had yet another delicious fish dinner (except for Russell who had a burger made from Maui beef, and Julia who had chicken strips as always).  Then we went back to the hotel to pack as we had to leave at 7 am for the airport the next day.

We had been monitoring Lala’s path and progress throughout the day -- still a tropical storm but predicted to be a hurricane by the time it made landfall on the big island --  and contemplated trying to fly home on Friday, but all the predictions said we should be just enough ahead of the really strong winds so we decided to proceed as planned.

Miscellaneous tropical drinks we experienced on Maui

We saw lots of chickens/roosters/hens on the island too

Saturday, August 15
When we first planned the trip, our plan had been to spend the day in Maui and fly out at night, but Jourdan really wanted to see Pearl Harbor so a couple months ago we changed our flights home to flying out of Honolulu, and booked flights for this morning from Maui to Honolulu.  It is a good thing we did, because our original flight home from Maui for Saturday night was canceled because of the storm.  It was intermittently REALLY windy and rainy in Maui as we were leaving but we made it out no problem!

Tropical storm Lala made some pretty rainbows

The flight from Maui to Honolulu was short, it felt like we just reached elevation before we started our descent.  At the Honolulu airport, we stored our bags and then took a Lyft to Pearl Harbor.  We walked around the area and went into the submarine museum, and had reservations to take the boat over to the USS Arizona Memorial at 2:00. At around 1:30, the park ranger who was letting people in and out suggested we try to get on an earlier boat because of the storm, as he was worried the boats would be cancelled.  So we did.  I think we all felt the solemnness of the memorial, where the majority of bodies of people on the ship were never recovered, and we thought about how it must have felt to be a survivor when most of your colleagues weren't.  

After we went back to the island, we explored more of the museums, and then when we were done we went to a restaurant right next to the memorial for a bite to eat (it was not good), and then to the airport.  We still had several hours until our flight, but Honolulu was pretty eerily quiet with people getting ready for the storm, and it was raining by then, and since we didn't really know the island or what we might do for a brief time, we just went to the airport.  Which was also eerily quiet because so many flights had been cancelled -- when we got to security there was no one there (seriously, no one) and the TSA agents were just waiting for us.

On a submarine

USS Arizona Memorial

All the flight screens looked like this -- so many cancellations!

We know that Maui was getting hit with Lala as we were leaving Honolulu, and we were thinking of all the kind people we had met all week.  Thankfully, we made it out of Honolulu without any issue, and made it home the next day.  Hopefully we all made memories to last a lifetime -- I know I did.