People ask me this constantly. I’ve visited Hawaii 40+ times over the past 20 years and I’m a Certified Hawaii Destination Expert. And still: “but what do YOU do when you go?”
So here it is. February 2026. My 12-year-old son and me, four days in Maui after five back-to-back work days on Oahu. That Oahu trip post is posted here.
This wasn’t a packed itinerary trip. It was intentionally slow. One big activity per day, good food, a lot of pool time, and one very memorable rainy luau. That’s it. And it was one of the better Maui trips I’ve had in years.
If you’re mid-planning and feeling buried, my free 7-day Maui email course is a good place to start. Or grab the Maui Family Travel Guide if you want everything in one place.
Day 1: Rental Car Drama, Fish Tacos, and the Hyatt
We flew in from Oahu and landed at OGG around 9:45am. Bags, the little tram to the rental car facility, the usual.
I was already nervous about Thrifty before I even got to the counter.
On Oahu, they had rented us a car with expired plates and then tried to convince me it wasn’t a problem.
This time, the agent told me the car I reserved “didn’t have trunk space” and I needed to upgrade. I said we were two people with minimal bags and asked for the smallest available car.
She put us in something four levels above what I originally booked and charged me more for it.
I won’t be renting from Thrifty again.
If you’re renting a car in Maui, I always recommend booking through Discount Hawaii Car Rental.
They work with multiple rental companies so you actually have options. I made the mistake of choosing Thrifty when I should have picked one of their other options.
Our first stop was someone’s house in Ha’ikū to pick up a haku lei I ordered for a photo shoot the next morning.
Then we drove to Coconut’s Fish Cafe in Kihei. Best fish tacos in Maui, in my opinion.
My son was in a burger mood so he went next door to Peggy Sue’s Maui and came back with a burger, fries, and an Oreo milkshake and was very pleased with himself.
We checked into the Hyatt Regency Maui in Ka’anapali around 1pm. I booked this stay on points, which meant the resort fee was waived. That’s a real savings at this property.
The room wasn’t ready until 4pm, so we dropped our bags and found Waikomo Shave Ice at the resort.
I’ve been going to Waikomo since they were a tiny stand on Kauai, so seeing how much they’ve grown was genuinely cool. The shave ice was great.
Our room was actually ready before we finished eating, so we went up, settled in, and spent about 30 minutes troubleshooting the wifi. Hotel staff fixed it in minutes via text, which I was impressed by.
Then I went to the resort shops for snacks and drinks so we could decompress. After five intense days on Oahu, decompressing was the whole plan.
We did in-room dining that night. I got the fish and chips. My son ordered a soft pretzel listed at $22, which made me blink. Then it arrived and it was genuinely the size of a small dog. Okay, fine.
Day 2: 5am Wake-Up, Flytographer, Maui Ocean Center, and a Waterslide Situation
I set my alarm for 5am because we had a 7am photo shoot in Wailea. Hair, makeup, and then I realized the dress I bought had no adjustable tie in the bust area like I thought it did.
So we made a pit stop at Long’s Drug Store for safety pins at 6am. This is the extremely glamorous life of a content creator.
I had booked a Flytographer session with a photographer named Nicole. This was my third Flytographer shoot on Maui.
I told her I needed some usable work photos but also wanted real ones with my son.
He’s 12 and in full tween mode, so I made him a deal: he didn’t have to be in all of them.
By the end of the hour he told me it “wasn’t so bad” and admitted he liked climbing on the rocks. High praise from a 12-year-old.
If a family photo shoot in Hawaii has been on your list, Flytographer is worth booking. First-time clients save $20 with my link.
The photos came back the next day, which I still find kind of unbelievable.
After the shoot we found Sweet Hula, an acai bowl food truck in South Maui Gardens. I’d read good things and it delivered.
They have premade bowls or you can build your own from a really long topping list. Both of us were happy.
Then we drove to the Maui Ocean Center in Ma’alaea. I had press tickets for this visit. It had been years since I’d last been (my kids were little the first time).
A huge local school field trip was there the same day so it was busier than I expected, but it made the place feel alive.
The highlights: sea turtles up close, baby sharks, and the walk-through tunnel.
You’re standing underneath sharks, manta rays, and tropical fish on all sides. It’s one of those experiences where you just kind of stop talking.
Also new since my last visit: an Ululani’s Shave Ice inside the aquarium. We spent about a third of our total visit waiting in that line. They make shave ice in batches so it moves slowly. Still did it.
The gift shop is massive and has actual nice things in it, not just magnets.
We grabbed cheaper snacks at Safeway on the way back to the resort and spent the rest of the afternoon at the Hyatt pool. I read on my Kindle (a non-negotiable for me on Hawaii trips).
My son went down the waterslide so many times he eventually lost his glasses in the pool. He spent 30 minutes searching for them underwater. He found them.
He was completely cooked after that and didn’t argue when I suggested snacks for dinner and lights out early.
I was asleep by 7pm.
Day 3: Cabana Day and a Luau in the Rain
My son had been counting down to this day since we booked the trip.
I went out at 7am to walk the resort and get photos and video for the blog and podcast.
Grabbed an iced chai from Honolulu Coffee Company in the lobby on my way back.
Their espresso program is solid and it’s a nice perk of staying at this particular property.
At 9am we headed to our cabana. Number 13, right next to the pool.
The Hyatt comped the cabana, lunch at Umalu, and our luau tickets as part of my press stay, and I want to be upfront about that.
That said, if you’re paying out of pocket, a cabana day at the Hyatt Regency Maui is genuinely one of the more relaxing ways to spend a Maui afternoon.
My son found pool friends within about 10 minutes. He never asked their names. They played for three hours.
I ordered poke nachos and a virgin piña colada from Umalu and got my son a plain burger.
I sat in the shade reading while my Flytographer photos came through in my inbox. That’s a pretty good afternoon.
We headed up around 2pm to clean up before the luau. That evening we went to the Drums of the Pacific Luau at the Hyatt, also comped.
And then it rained.
I’m from Seattle so I’m not scared of rain. But I showed up in a sundress. They handed out plastic ponchos along with kukui nut leis and mai tais (my son got POG juice) and we settled into our VIP seats.
The pre-show was music and hula, no hands-on activities. The buffet food was better than average for a luau buffet, but eating outside in the rain is a challenge and I gave up after about 10 minutes.
The show itself was really good. Dancing from Hawaii, Samoa, Tahiti, New Zealand, and Tonga.
I think they condensed it because of the weather because we were done by 7pm instead of the advertised 8pm.
I didn’t mind.
By the end I was damp even with the poncho and I went straight upstairs to dry off with the hair dryer.
I’ve got an honest review here. If you’re comparing Maui luaus right now, you can browse options on Viator or Get Your Guide.
Not sure which luau is right for your family? That’s exactly the kind of thing I sort out in my Hawaii travel consultations. A lot of families waste money on the wrong one.
Day 4: Whales, Cafe O’Lei, Iao Valley, and a Very Long Airport Wait
A few things were going on with this day before we even got out of bed.
Our flight home was an 11:30pm redeye. I booked it specifically to save around $1,000 because Hawaii airfare in February 2026 was genuinely painful.
At one point I was looking at $2,000 per person. The redeye was the only option that made sense.
Also, the TSA PreCheck and Global Entry programs had been “paused” by the government starting that day, so I was stressed about airport wait times for an already-late flight.
Both were running fine when we got there. It turned out to be a non-issue, but I didn’t know that yet and it had me anxious all day.
The weather forecast showed 90% rain across all of Maui, which knocked out my backup plans of beach or pool time. Maui weather rarely does what the forecast says, though.
The Hyatt gave us a late checkout at noon, which was a huge help. I spent the morning walking the property for content and stopped in my tracks when I spotted whales just off the coast in front of the hotel.
Humpback whale season in Maui runs roughly November through May. Seeing them from the shoreline on your last morning is not something you forget quickly.
I made a reservation at Cafe O’Lei at the Plantation in Waikapu for 12:30pm, calling around 11am that morning and getting right in.
This is one of my favorite restaurants on Maui. The setting is beautiful and the sautéed mahi mahi is one of my most reliably great Maui meals.
If you want to eat here, don’t wait to book. Walk-in wait times can be long.
From there we drove to the Maui Pineapple Store in Hali’imaile. They sell airport-ready Maui Gold pineapple, packaged so it actually clears TSA, and it’s some of the best pineapple grown in Hawaii.
They also have Maui pineapple tours. We did it a few years ago and I highly recommend it.
Worth a stop if you’re heading upcountry anyway.
We still had hours before our flight, so we drove to Makawao Town (mostly closed, it was Sunday, but still worth a walk), and hiked part of the Makawao Forest Reserve before turning back.
After that, we drove out toward ‘Ulupalakua Ranch and Store mostly for the scenic drive through upcountry. The views up there, even on a cloudy day, are genuinely beautiful.
Then Iao Valley State Park. You need a timed entry reservation to visit. Book through Hawaii’s DLNR State Parks reservation site before your trip.
It’s a quick stop but one of my favorite places on all of Maui. The Iao Needle, the green cliffs, the stream. It’s beautiful and it’s free once you pay the $5 per person green fee.
After that: Walmart for airplane snacks and drawing supplies for my son, Foodland for spam musubi, Costco Gas before returning the rental car, and then the airport about 3.5 hours early because there was genuinely nothing else open in town at that hour.
Alaska Airlines wasn’t open for 30 minutes after we arrived so we got in line and waited. PreCheck and Clear were both running smoothly. We made it home.
What I’d Tell You If You Were Planning This Trip
A slower Maui trip is worth considering. Most families I work with in my Hawaii travel consultations try to fit too much in and end up exhausted.
One main activity per day, a good meal, and actual rest time. That’s the trip people look back on and say was their favorite.
Skip Thrifty. Twice now they’ve created problems at pickup. I’m done with them. Discount Hawaii Car Rental is where I send people and where I’ll be booking from now on.
If you’re deciding between Maui and Oahu, I did a whole podcast episode on exactly that.
Episode 87 of Hawaii Travel Made Easy: Maui vs Oahu 2026: The One Thing Everyone Gets Wrong When Choosing.
It’s one of the most common questions I get in consultations and the answer usually surprises people.
For where to stay, episode 71 covers the best areas to stay on Maui, Ka’anapali, Wailea, Kihei, and beyond.
The Hyatt held up really well for us and the points redemption made it a great deal, but it’s not the right fit for every family.
And if you’re just starting to plan a Maui trip from scratch, episode 47 walks through how to plan a trip to Maui step by step.
Common Questions About Planning a Maui Trip
Do you need a car in Maui?
Yes, in almost every case. Maui doesn’t have reliable public transportation between areas, and most of the things worth doing are spread out across the island.
Book early because rental car availability in Maui gets tight, especially in winter. I use Discount Hawaii Car Rental.
What is Maui’s green fee?
Hawaii charges a green fee (officially the Hawaii Transportation Fee) for visitors entering certain state parks.
As of 2025-2026, it’s $5 per person at places like Iao Valley. You pay this when you make your timed entry reservation through the DLNR State Parks site.
Do you need reservations for Iao Valley State Park?
Yes. Timed entry reservations are required and you book them in advance through Hawaii’s DLNR State Parks reservation system. Walk-ups are not guaranteed entry.
When is whale season in Maui?
Humpback whales are in Hawaiian waters roughly November through May, with peak season in January through March. February is one of the best months to spot them. We saw them right from the Hyatt shoreline on our last morning.
Is the Maui Ocean Center worth it for kids?
Yes, especially for the walk-through shark tunnel. Plan at least 2 hours. If Ululani’s is still open inside (it was when we visited in February 2026), factor in extra time for that line.
Is a Flytographer shoot worth it in Hawaii?
If you want photos you’ll actually use, yes. The photographers are local, they know the best spots and light, and the turnaround is fast.
First-time clients save $20 with my link. This was my third shoot with them on Maui and I’ve been happy every time.
Ready to Plan Your Own Maui Trip?
As a Certified Hawaii Destination Expert and professional tourist with 40+ visits to the islands, Maui is one of my favorite trips to help families plan. It’s also one of the easier ones to get wrong if you’re not careful about the details.
The free 7-day Maui email course covers the basics: neighborhoods, hotels, activities, and logistics.
If you want someone to look at your specific itinerary and catch the mistakes before you make them, my one-on-one Hawaii travel consultations are $149 and one hour.
Most families tell me they saved at least that much by not booking the things they were about to book.
For more honest talk about Maui and Hawaii in general, subscribe to the Hawaii Travel Made Easy podcast. It’s where I say the things that don’t always make it into the blog.