Traveling to Maui for Christmas sounds pretty idyllic.
Traveling to Maui for Christmas with a three-year-old and a six-month-old?
Still idyllic.
Just considerably less relaxing.
We spent a week on Maui over Christmas, staying in a condo complex just north of Kaanapali Beach. With two very young kids, having the extra space of a condo made sense, and West Maui gave us easy access to beaches, snorkeling and day trips without requiring us to constantly pack up and change hotels.
Over the course of the week, we explored Kaanapali, Napili Bay, Kapalua and the Nakalele Blowhole.
We saw sea turtles.
We watched humpback whales offshore.
We snorkeled among tropical fish.
And we made the very questionable decision to wake up two small children around 4:00 in the morning and drive across Maui toward Hana in the dark.
That turned out to be one of the best decisions of the trip.
Christmas in Hawaii
There are worse places to spend Christmas.
Warm weather.
Palm trees.
The Pacific Ocean.
Whales offshore.
Kids playing outside instead of being bundled into winter clothes.
Maui is already a special place, but there was something particularly memorable about being there as a family during the holidays.
And because our kids were only three years old and six months old, this wasn’t going to be an adventure-packed Hawaiian itinerary.
That was fine.
At those ages, you need a home base.
A pool.
A beach.
A kitchen.
Nap flexibility.
And enough interesting places nearby that you can explore without turning every day into an expedition.
West Maui worked extremely well for that.
Kaanapali: Beautiful, But Not Really Our Style
I’ll probably lose a few people here.
Kaanapali was overrated.
To be clear, Kaanapali Beach is objectively beautiful.
Long stretches of sand.
Clear water.
Excellent snorkeling.
Beautiful resorts.
Easy access to restaurants and shops.
It’s popular for a reason.
But the main resort area around Black Rock felt too touristy and manufactured for us.
This was Hawaii packaged as a resort destination.
Large hotels.
Crowded beach.
Lots of people.
Everything convenient.
Everything polished.
And not much sense that you’d discovered anything yourself.
If that’s what you want from Maui, Kaanapali is excellent.
It just wasn’t our favorite part of the island.
Ironically, knowing what I know now, I’d probably stay there next time.
Why I’d Stay at the Westin Next Time
This is one of those travel opinions that sounds contradictory until you’ve traveled with small children.
I thought Kaanapali was too touristy.
And next time, I’d probably stay at The Westin.
Why?
Because traveling with a six-month-old and three-year-old changes the equation.
With kids that young, convenience is a luxury.
Having a great pool, beach, restaurants and everything else you need within a few minutes of your room is enormously valuable.
You don’t necessarily need your hotel to be the most authentic experience on the island.
You need it to make family life easy.
We were only a short drive away, so we spent time around Kaanapali anyway.
In retrospect, I’d rather have simply stayed there, enjoyed the resort’s pool and beach when we wanted an easy day, and then used the car to explore the parts of Maui we liked more.
Sometimes the best hotel isn’t in your favorite neighborhood.
It’s the hotel that makes the rest of the trip work.
The Snorkeling Was Excellent
The crowds around Black Rock weren’t my favorite.
The snorkeling was.
We saw a ton of fish and sea turtles in the water around Kaanapali.
For someone who wants easily accessible snorkeling without turning it into a major excursion, it’s difficult to argue with the convenience.
Walk into the ocean.
Put your mask on.
Start swimming.
That’s pretty hard to beat.
And when you’re traveling with little kids and one parent may need to stay onshore while the other snorkels, easy access matters even more.
Napili Bay
Just north of Kaanapali is Napili Bay, which offered a different atmosphere.
Smaller.
More intimate.
Less dominated by enormous resorts.
This is one of the benefits of staying in West Maui.
You don’t need to commit to one beach for the entire week.
Drive a few minutes north and the experience changes.
Keep driving and it changes again.
Which eventually brought us to my favorite area on this side of Maui:
Kapalua.
Kapalua
If Kaanapali felt a little too manufactured for us, Kapalua felt much closer to what we wanted from Maui.
Beautiful coastline.
Green landscape.
Excellent snorkeling.
Turtles.
Whales.
And enough development to make everything comfortable without feeling like you’re in the middle of a giant resort complex.
The snorkeling here was particularly good.
If your children are old enough to actually snorkel and enjoy the water, I’d put Kapalua high on the list.
We saw plenty of marine life, including sea turtles.
But during winter, there was something else offshore.
Humpback Whales
Christmas falls right in Maui’s humpback whale season.
And we saw them.
A lot of them.
The waters around Maui are an important winter destination for North Pacific humpbacks, which migrate to Hawaii’s warm waters to breed, give birth and nurse their calves.
Around Kapalua, we’d look toward the ocean and see whales offshore.
A blow.
A splash.
Sometimes more.
It reached the point where spotting another humpback became almost casual.
Then you remind yourself:
That’s a humpback whale.
There’s nothing casual about it.
Walking the Kapalua Coast
One of the easiest things we did was also one of the most enjoyable.
There’s a relatively short coastal walking trail around Kapalua that provides beautiful views over the water.
With two little kids, this was exactly the kind of activity we needed.
No elaborate preparation.
No full-day commitment.
No major hike.
Just get outside and walk along the coastline.
During whale season, keep looking toward the water.
You may have company.
Nakalele Blowhole
Farther north, the coastline gets considerably more rugged.
We drove up toward the Nakalele Blowhole, where waves force seawater through an opening in the volcanic rock and send it shooting into the air.
The landscape around this part of Maui feels very different from the manicured resort areas farther south.
Rugged lava rock.
Wind.
Powerful surf.
Open coastline.
It’s beautiful.
It’s also somewhere to be cautious, particularly with children. The ocean here isn’t a swimming pool, and getting close to a blowhole or wet rocks for a better photo isn’t worth the risk.
We enjoyed the scenery and kept an appropriate distance.
The Road to Hana With a Baby and a Three-Year-Old
Then there was Hana.
Everyone tells you the Road to Hana is about the journey.
They’re right.
But we approached it almost completely backward.
And I would absolutely do it the same way again.
The typical strategy is to leave in the morning and stop repeatedly along the way.
Waterfall.
Pullout.
Hike.
Food stand.
Another waterfall.
Another pullout.
By the time you actually reach Hana, you’ve spent most of the day getting there.
That sounded exhausting with a three-year-old and six-month-old.
So we developed another plan.
Get to Hana first.
4:30 A.M.
We left around 4:30 in the morning.
Yes.
With a three-year-old.
And a six-month-old.
There are moments in family travel when you have to commit fully to an idea and hope you haven’t made an enormous mistake.
This was one of them.
Our goal was to drive toward Hana before the day’s traffic developed and reach town early enough for breakfast.
Then, instead of making 15 stops, we’d choose the two or three things we actually cared about and visit those as we worked our way back.
It worked perfectly.
Breakfast at Hana-Maui Resort
We reached Hana in time for breakfast at the Hana-Maui Resort.
After driving across the island before sunrise, sitting down for breakfast overlooking the tropical landscape felt like we’d already accomplished something significant.
And we had.
We were in Hana.
Early.
Before the crowds.
Instead of spending the entire morning wondering when we’d finally arrive, we’d made the destination our starting point.
We could eat.
Relax.
And then explore.
Hana Was Worth It
I had heard plenty of conflicting opinions about the Road to Hana.
Too long.
Too many turns.
Too crowded.
Overrated.
Difficult with children.
I understand all of those criticisms.
But for us?
Hana was amazing.
Completely worth the effort.
The eastern side of Maui feels different from the resort areas of West Maui.
Lush.
Wet.
Wild.
Tropical.
The road itself winds through dense vegetation, across bridges and past waterfalls as the coastline appears and disappears beside you.
This was the Hawaii I wanted to experience.
Black Sand Beach
One of our priorities was the famous black sand beach at Waiʻānapanapa.
The contrast is incredible.
Black volcanic sand.
Deep blue water.
Green tropical vegetation.
Dark lava cliffs.
After spending several days around Maui’s traditional golden beaches, it almost feels like you’ve arrived on another island.
This wasn’t somewhere we wanted to rush.
And because we’d been selective about our stops, we didn’t have to.
Red Sand Beach
We also wanted to see Red Sand Beach near Hana.
Again, completely different.
The red volcanic cinder surrounding the small cove creates one of the most unusual coastal landscapes on Maui.
It was exactly the kind of place that made the long drive worthwhile.
One important caveat: access to Red Sand Beach can be difficult and potentially hazardous, particularly with young children. Conditions and access can change, so I wouldn’t recommend treating our experience as an automatic endorsement to bring babies or toddlers down the trail.
The lesson isn’t that everyone needs to visit exactly the same places we did.
It’s to choose a few places that matter to you.
Don’t Try to Stop Everywhere
This is probably my strongest Road to Hana advice.
You do not need to stop at everything.
In fact, I think trying to stop at everything can ruin the experience.
There are countless waterfalls, viewpoints, beaches, trails, roadside stands and scenic pullouts.
You could spend days exploring this side of Maui.
You cannot meaningfully experience all of it in one day.
So don’t try.
We picked a few priorities.
Black Sand Beach.
Red Sand Beach.
A great meal overlooking the ocean.
Everything else was optional.
That transformed the drive.
Instead of constantly worrying about the next stop, we could enjoy the places we’d chosen.
Stay in Hana?
Without kids?
Absolutely.
If I returned to Maui without young children, I’d seriously consider spending at least one night in Hana.
Driving there and back in a single day is possible—we did it—but staying overnight would allow you to experience the area after most day-trippers leave.
You could slow everything down.
Explore more.
Have dinner.
Wake up in Hana.
And tackle another stretch of coastline the next morning.
With a baby and a three-year-old, however, changing hotels and moving all our stuff for one night wasn’t worth it.
Our absurdly early departure worked better for us.
What I’d Do Differently Next Time
Our week taught me a lot about how I’d structure another family trip to Maui.
I’d stay at the Westin in Kaanapali.
Not because Kaanapali was my favorite part of Maui.
It wasn’t.
I’d stay there because the resort, pool, beach and location make family travel easy.
Then I’d leave Kaanapali whenever we wanted something different.
I’d spend more time around Kapalua.
If the kids were old enough, we’d snorkel together there.
I’d walk the coastal trail and look for whales.
I’d return to Napili.
And I’d absolutely go back to Hana.
If I Went Back Without Kids
That itinerary would look different.
I’d spend a night or two in Hana.
I’d take more time exploring the eastern side of Maui.
I’d make more stops.
I’d hike.
I’d let the Road to Hana become a two-day experience instead of a very long day trip.
And I’d still get up early.
Maybe not 4:30-with-a-six-month-old early.
I’ve already proven that point.
Maui With Little Kids
Traveling with a baby and toddler isn’t easy.
You’re carrying more stuff.
Schedules matter.
Naps matter.
Meals matter.
A simple beach trip somehow requires the logistics of a minor military operation.
But that doesn’t mean you need to stop traveling.
You adapt.
We skipped long museum-style attractions because there weren’t any we needed to see.
We spent time at beaches.
We walked.
We snorkeled in shifts.
We watched whales.
We built in downtime.
And when we really wanted to do something ambitious, like Hana, we designed the day around our kids rather than pretending they weren’t coming.
Leaving at 4:30 a.m. sounds crazy.
With our kids sleeping through part of the drive and the roads relatively quiet?
It actually made the day easier.
Final Thoughts
Our Christmas week in Maui wasn’t perfect.
Kaanapali was more commercial than I expected.
Traveling with a three-year-old and six-month-old required constant adjustment.
And the Road to Hana demanded one of the earliest vacation wake-up calls I’ve ever voluntarily scheduled.
But some of my strongest memories of Maui came from those decisions.
Watching humpback whales offshore near Kapalua.
Swimming with turtles.
Walking along the coast.
Seeing black volcanic sand surrounded by tropical jungle.
Reaching Hana early in the morning and sitting down for breakfast knowing we’d beaten most of the day’s traffic.
And watching our two little kids experience Hawaii with us.
If I went back tomorrow, I’d change the hotel.
I’d spend even more time around Kapalua.
I’d still think Kaanapali was overrated.
And I’d still wake up ridiculously early for Hana.
Because if there’s one thing I’d tell someone debating whether the Road to Hana is worth all that effort:
Go.
Just don’t try to see everything.
Pick the places you really want to experience.
Get there before everyone else.
And give yourself enough time to actually enjoy them.
Hana isn’t something to check off a Maui itinerary.
It’s the part of Maui that made us want to come back.
