Are you in the early stages of planning a Maui family vacation this year? Keep scrolling for my kid-friendly 5 days in Maui itinerary!
This 5 days in Maui itinerary was written by Hawaii travel expert Marcie Cheung and contains affiliate links, which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.
TL;DR: What You’re Really Doing
Day 1: Land, check in, beach. That’s it.
Day 2: Wake up stupid early for Haleakala sunrise, nap all afternoon
Day 3: Road to Hana (bring ALL the snacks)
Day 4: Ocean time + luau
Day 5: Last beach fix, fly home sad
Real Budget: $8,500-10,000 for a family of four including flights. Yeah, it’s expensive. Hawaii visitors spent an average of $270-280 per person per day in 2025.
When to Go: April-May or September-November if you want smaller crowds and don’t want to sell a kidney to afford your hotel.
I’ve been going to Maui since I was 16. My grandmother lived part-time on Kauai, my mom lives there now, and I’ve been to Hawaii over 40 times total.
Maui specifically? About a dozen trips.
After 20+ years of hula dancing, becoming a certified Hawaii Destination Specialist, and dragging my two boys to the islands repeatedly, I’ve figured out what actually works for families.
This isn’t the perfect Instagram itinerary where everyone smiles at 4am.
This is the version where someone forgot their warm jacket (again), another kid announces he has to pee right when you find the perfect sunrise spot, and you still have an amazing time.
Where to Stay (This Matters More Than You Think)
Quick stat: Maui welcomed 2.35 million visitors in 2024, recovering from the post-fire slump. Hotel occupancy in West Maui hit 61.2% in August 2025, up from 50.8% the year before.
Your hotel basically determines your whole vibe, so don’t screw this up.
West Maui (Kaanapali/Kapalua)
The beaches are gorgeous. Kaanapali Beach Walk means you can actually walk to dinner without getting back in the car. Which is huge when you’re on vacation and nobody wants to drive anywhere.
But here’s the thing about Lahaina that you need to know:
Front Street isn’t there anymore. The August 2023 fires destroyed most of historic Lahaina.
The county’s still finishing infrastructure work (railings, sidewalks, seawall repairs) with completion expected July 2026.
After that, commercial buildings can start rebuilding. We’re talking years, not months.
Some businesses have come back in other parts of Lahaina. Sale Pepe pizzeria reopened on Kupuohi Street in March 2025 (first restaurant back). Old Lahaina Luau is operating again.
But that walkable Front Street with all the shops and restaurants? Not happening on this trip.
It makes me sad every time I think about it. That was such a special place.
West Maui is about 45 minutes from the airport and farther from Haleakala.
Find West Maui hotels on Expedia
South Maui (Wailea/Kihei)
This is where I usually tell first-timers to stay.
Wailea has the big fancy resorts. Four Seasons, Grand Wailea, Fairmont Kea Lani.
They have kids clubs, seventeen pools (okay not literally seventeen but it feels like it), and you’re right on the beach.
Kihei is the budget version. More condos, more local feel, less fancy but still great beaches.
South Maui is sunnier and drier than West Maui. You’re only 20-30 minutes from the airport, which is clutch on arrival and departure days when everyone’s grumpy and tired. The drive to Haleakala is shorter too.
Downside: You’re farther from Road to Hana (adds about 30 minutes each direction).
West vs South Maui Side-by-Side
| West Maui | South Maui | |
|---|---|---|
| Best beach for kids | Kaanapali (calm, swimmable) | Wailea Beach (super calm) |
| Walkable restaurants | Yes in Kaanapali | Not really in Wailea, yes in Kihei |
| Drive to airport | 45 min | 20-30 min |
| Drive to Haleakala | 1.5-2 hours | 1-1.5 hours |
| Weather | Can get rainy | Sunnier, drier |
| Our pick | When we want walkability | When we want convenience |
For your first trip? Go South Maui. Just trust me on this one.
Check out my full Maui travel guide if you want way more detail on hotels.
Day 1: Just Get There and Breathe
Afternoon: Land in Maui
Your flight gets in. Everyone’s tired. Someone’s hungry. Another person’s cranky because their tablet died somewhere over Nevada.
Rental car: I book through Discount Hawaii Car Rental every single time. They compare all the companies and I’ve saved hundreds of dollars this way.
Drive to your hotel.
Don’t stop for groceries. Don’t try to squeeze in a beach you pass on the way. Just get to the hotel, check in, and let everyone decompress for a minute.
Beach or pool.
This is not the day for ambition.
Last time we arrived, my youngest wanted to jump in the pool immediately even though it was like 5pm and we hadn’t eaten since breakfast. Fine. Whatever. He jumped in the pool in his travel clothes and I ordered pizza to the room.
Sometimes that’s what vacation looks like and it’s totally fine.
Dinner:
If you’re in Kaanapali, Duke’s or Leilani’s are both right there. In Wailea, Monkeypod Kitchen (SO good, always packed).
Or honestly? Grab poke from Foodland and eat it on your lanai. We did that last trip and my boys thought it was the coolest thing ever. Saved $100 too.
Pro tip: Everyone’s still on mainland time. Put the kids to bed early so they’re not complete monsters tomorrow at 2:30am.
Day 2: Haleakala Sunrise (Pack Like You’re Going to Alaska)
2:30am: Wake Up
I’m not a morning person. At all. But Haleakala sunrise is genuinely worth the pain.
You need to leave your hotel by 3:00-3:30am depending on where you’re staying.
Critical info:
- Book sunrise reservation 60 days in advance on Recreation.gov
- Costs $1 per vehicle
- Required 3:00am-7:00am
- Sells out FAST
- Park entrance is $30 (separate fee, good for 3 days, credit card only)
- Drive time: 1.5-2 hours from West Maui, 1-1.5 hours from South Maui
About staying warm (THIS IS IMPORTANT):
The first time I took my boys to Haleakala, I completely underestimated how cold it gets at 10,000 feet. They were absolutely freezing and insisted on staying in the car almost the entire time. It was miserable. I felt like the worst mom.
Now we come prepared and it’s a totally different experience.
Bring:
- Hand warmers (these ones on Amazon – stick them in jacket pockets before you leave the hotel)
- Puffy coats (yes, really)
- Beanies
- Long pants
- Gloves
- Blankets from your hotel room
Temps at the summit are typically 40-45°F but with wind chill it feels WAY colder.
I know this is Hawaii. I know you’ll look ridiculous packing winter gear. Do it anyway.
4:30am-ish: Sunrise
Get there early enough to park and find a spot at the summit. Even with reservations, parking fills up.
Bundle up. Grab your coffee (bring it from the hotel or you’re out of luck). And wait.
The sun rising above the clouds at 10,023 feet is absolutely stunning. It’s so quiet except for whispers and camera clicks. There’s something really special about watching this with your kids. Even my tween thought it was cool.
Stay at least 20 minutes after sunrise. The colors keep changing. The landscape keeps revealing itself as it gets lighter. Most people leave right away and they miss the best part.
6:30am: Explore a bit
Drive to Kalahaku Overlook for incredible crater views. Stop at Haleakala Visitor Center (bathrooms, thank goodness).
If you’re feeling ambitious, hike part of Sliding Sands Trail.
Spoiler: After waking up at 2:30am, nobody’s feeling ambitious. We usually walk like 50 feet down the trail, take some photos, and turn around.
8:30am: Head down
Those switchbacks are no joke. Drive carefully.
Stop at Kula Lodge food truck for breakfast on the way down if you want. Good pancakes, great view.
Rest of the day: Beach time
Go back to your hotel. Naps are mandatory. Spend the afternoon at the beach or pool.
We usually order pizza this night and everyone’s in bed by 7pm.
Want to learn more about what to expect? I cover all this in my free email course on traveling to Hawaii like a pro.
Day 3: Road to Hana (The Best and Longest Day)
6:00am: Leave early or regret it
The Road to Hana is 64 miles of winding coastal road. 620 curves. 59 bridges. Absolutely stunning. Also absolutely exhausting if you leave late and get stuck in traffic.
Pack:
- SO many snacks (I’m talking an entire grocery bag)
- Water bottles
- Dramamine (someone will get carsick, trust me)
- Bathing suits and towels
- Reef-safe sunscreen
- Full tank of gas
Route:
Most people do Paia → Hana → turn around. That’s about 100 miles round trip, minimum 4-5 hours of driving plus stops.
Some people loop around the southern part of the island past Hana. Don’t do this with kids. The road gets rougher, rental car companies hate it, and you’re adding HOURS to an already long day.
Just turn around and come back the way you came.
Where to actually stop:
Twin Falls (Mile Marker 2)
First big stop. Easy waterfall walks. Gets super crowded so arrive early. There are fruit stands here too.
Garden of Eden (Mile Marker 10)
This is our favorite stop on the entire Road to Hana.
It’s a botanical garden with absolutely stunning waterfall views. They charge admission ($20 per adult, kids under 16 free) but it’s 100% worth it. The trails are well-maintained, the bathrooms are clean, and the views are incredible.
You’re looking at the same waterfalls from Jurassic Park which my kids thought was the coolest thing ever.
We usually spend about an hour here. The trails aren’t too hard but feel like an adventure.
Halfway to Hana (stand with snacks and banana bread)
We ALWAYS stop for banana bread. It’s become a total family tradition. Get the chocolate chip macadamia nut if they have it.
Wai’anapanapa State Park (Mile Marker 32)
Black sand beach, lava caves, dramatic coastal views.
You need a parking reservation ($10 per vehicle). Book it when you book your Haleakala sunrise.
The beach is beautiful but the water can get rough. Watch your kids closely if they go in.
Hana Town
Stop for lunch. Hana Ranch has burgers. Or grab food from a food truck. Bruddah Hutts has the best BBQ I’ve ever had.
Honestly, by this point everyone’s tired and just wants to get back in the car.
Past Hana (if you want):
Wailua Falls and Pools of ‘Ohe’o are beautiful. The pools are in Haleakala National Park so your 3-day pass from Day 2 works. Swimming isn’t currently allowed but the hike and views are still worth it.
We usually turn around at Hana town because everyone’s done.
Drive back:
Just as long but different light for photos. We make fewer stops on the way back because we’re all ready to be done.
Try to get home by 5:00-6:00pm. Everyone will be exhausted.
Dinner: Order in. Nobody has the energy to go out.
I created a whole free email course just for planning a Maui trip that goes way deeper into Road to Hana strategy and stops.
Day 4: Ocean Time & Luau
Morning: Pick your water adventure
Option 1: Molokini Crater snorkel tour (this is what we usually do)
Molokini is a partially submerged volcanic crater about 3 miles offshore. The snorkeling is incredible. Super clear water, tons of fish, sea turtles.
Tours leave around 6:30-7:00am (yeah, another early morning). They include breakfast, lunch, snorkel gear, and run about 4-5 hours.
Book in advance through Viator or Get Your Guide. Pride of Maui and Trilogy are both good.
Cost: $100-150 per adult, $60-100 per kid.
Option 2: Atlantis Submarine
If snorkeling isn’t your thing (or you have really young kids), the Atlantis Submarine tour is back up and running after the fires.
I took my oldest on this when he was a toddler and he LOVED getting to see all the sea life without having to dunk his head underwater. It was perfect for his age.
Book through Atlantis Adventures.
Option 3: Maui Ocean Center
The Maui Ocean Center is always a hit, especially with younger kids. My youngest is obsessed with their touch pools. He could spend an hour just touching the same sea cucumber over and over.
And they just put an Ululani’s Shave Ice right at the ocean center! So you can do the aquarium and then get what’s honestly the best shave ice on Maui. Win-win.
Option 4: Beach day at Makena
If you’d rather skip organized tours, head to Makena Beach (Big Beach). It’s one of Maui’s longest beaches, gorgeous golden sand, great for body surfing.
Water can get rough so keep an eye on kids.
Note: Little Beach (accessed by a short trail over rocks) is clothing optional. FYI. Stick to Big Beach with the family.
Parking is free but fills up by mid-morning.
Option 5: South Maui beach hopping
Wailea Beach, Ulua Beach, Keawakapu Beach. All beautiful. All swimmable.
Starting in 2026, Kamaole Beach Parks I, II, and III have a new $10 parking fee for visitors. Residents park free and get exclusive access until 10am on weekends/holidays. Just so you know.
Afternoon: Rest and prep
Come back to the hotel. Shower off the salt and sand. Nap if you want. Get ready for the luau.
Evening: Luau time
Old Lahaina Luau is the most authentic luau on Maui. They focus on traditional Hawaiian culture and history, not the Vegas-style Polynesian revue thing.
All-you-can-eat Hawaiian food (kalua pig, poi, lomi salmon, haupia), open bar, beautiful show.
They reopened in 2024 after the fires with about 75% of their original staff. It was such a big deal for the community to have them back.
Book WAY in advance. They sell out constantly. Around $150-180 per adult, $95-115 per kid (ages 3-12).
Book through Hawaii Activities.
Get the early seating if you have young kids. The late show runs really late.
If Old Lahaina Luau is sold out:
- Te Au Moana (Wailea) – beachfront, really pretty
- Grand Luau at Honua’ula (Grand Wailea) – convenient if you’re staying there
- Drums of the Pacific (Kaanapali) – more touristy but still fun
Compare all of them on Get Your Guide or Viator.
Flytographer tip: If you want professional family photos in Hawaii, I’ve used Flytographer (save $20 with my link) for over 20 shoots now.
My first one was years ago on Maui with the whole family, and I’ve used them everywhere since.
Last Maui trip I did a solo shoot in Wailea just for myself because I wanted some nice photos. They make it so easy.
Day 5: Last Beach Fix & Go Home
Morning:
Depending on your flight time, squeeze in one more beach or pool session.
If you need souvenirs:
- Whaler’s Village (Kaanapali) – touristy but walkable
- The Shops at Wailea – fancy, good for browsing
- ABC Stores – everywhere, cheapest option for mac nuts and coffee
Lunch:
When I’m home in Seattle, I dream of the fish tacos at Coconut’s.
If you have time before the airport and you’re anywhere near Kihei, stop there. I’m not even kidding, I think about those fish tacos all the time.
Return the rental car:
Build in 20-30 minutes for this. The lines at Kahului Airport rental return can be long.
Fly home:
Hopefully everyone’s tan and happy. Probably also sad to leave.
What This Itinerary Skips (And Why)
Ulupalakua Ranch Store: Okay this isn’t on the typical tourist list but I LOVE going here. It’s the name of a song I used to dance hula to for years.
As soon as we pull in, I’m already singing it in my head and my body just starts doing the hula moves. My kids think I’m embarrassing. I don’t care.
It’s not critical for a first-time 5-day trip, but if you have extra time, drive up there. It’s beautiful and the ranch store has good sandwiches. It’s on the way to/from Haleakala.
Whale watching: If you’re here December-April, absolutely add this. Otherwise the whales aren’t here (they’re in Alaska).
Ziplining: Fun but takes half a day. Save it for a longer trip.
Helicopter tour: Expensive. And honestly, you’ll see incredible views from Road to Hana and Haleakala.
Golf: If you golf, you already know what to do.
When to Actually Go to Maui
Peak season (mid-December through March):
Most expensive. Most crowded. But best weather and whale watching.
Shoulder season (April-May, September-November):
This is when I tell people to go. Smaller crowds, lower prices, still gorgeous weather.
Summer (June-August):
Crowded because school’s out. Hotter, more humid, higher prices.
Fall (September-October):
Secretly my favorite time. Lowest prices, smallest crowds, warm water.
Quick stat: Maui recovered to 2.35 million visitors in 2024, down from 3.06 million pre-pandemic. So even “crowded” times aren’t as intense as they used to be.
If you’re unsure, here’s my full breakdown of how many days you really need in Hawaii.
What It Really Costs
Let’s be real about money:
- Lodging: $300-600+ per night
- Rental car: $60-100 per day
- Food: $150-200 per day for a family of four
- Activities: $100-300 per day
- Gas: $50-75 for the week
Total for 5 days without flights: $4,000-6,000+
Maui visitors spent an average of $634 per person per day in 2024. That’s dropped to around $270-280 per person per day in 2025. So for a family of four, you’re looking at $1,100+ per day all-in.
It’s expensive. It just is. Hawaii’s expensive.
If you want to save money, I have a free email course specifically about saving money in Hawaii.
Don’t Forget to Pack
Must-haves:
- Reef-safe sunscreen (it’s the law)
- Rash guards for everyone
- Hats and sunglasses
- Refillable water bottles
- Light jacket for AC and restaurants
- WARM clothes for Haleakala (puffy coats, beanies, gloves)
- Hand warmers from Amazon
- First aid kit with Dramamine
- Waterproof phone case
- Snacks for Road to Hana
- Get my complete packing list if you want more details.
Things I’ve Learned After 40+ Hawaii Trips
Book everything in advance. Sunrise reservations, luau tickets, snorkel tours. They all sell out.
Don’t overpack your days. You’re on vacation. Build in downtime. Some of our best memories are from afternoons where we just hung out at the pool.
Bring hand warmers to Haleakala. I’m saying it again because people ignore this and then they’re miserable.
Leave early for Road to Hana. 6:00am or earlier. Seriously.
Rental cars are more expensive than you think. Budget accordingly.
Your kids will be sandy. Embrace it. You can wash the sand out of everything later.
Take photos but also put your phone down. I’m still working on this one.
Respect the land and ocean. Don’t touch coral. Don’t chase turtles. Pack out your trash. Be a good visitor.
Need Help Planning?
Listen, I get it. Planning a Hawaii trip is overwhelming. There are seventeen million blog posts telling you what to do and they all say different things.
I’ve been helping families plan Hawaii vacations for years. I’m a certified Hawaii Destination Specialist, a professional tourist (my actual title), and I’ve been to Hawaii over 40 times.
If you’re feeling overwhelmed, I offer personalized Hawaii travel consultations where we’ll map out your entire trip together based on your specific family, budget, and travel dates.
I also host the Hawaii Travel Made Easy podcast where I answer real questions from families planning trips.
And I have free email courses for:
I also have complete travel guides for:
Your Questions Answered
Which Hawaiian island is best for first-timers with kids?
Maui. The beaches are amazing but actually swimmable (not like the North Shore of Oahu where the waves will eat your children). You can drive to waterfalls, volcanos, and rainforests. Everything feels accessible without being overwhelming.
Oahu is great too, especially if Pearl Harbor is on your list. But Maui has a more chill vibe.
How many days do you really need?
Five to seven days is perfect for families. Less than five and you’re rushing. More than seven and honestly you might want to add another island.
This 5-day itinerary hits all the big stuff without totally exhausting everyone.
Do I actually need a Haleakala sunrise reservation?
Yes. The park requires it for any vehicle entering 3:00am-7:00am. Book 60 days in advance on Recreation.gov.
You CAN visit after 7:00am without a reservation. But sunrise is the most spectacular time. It’s worth setting an alarm for.
Is Road to Hana worth it with kids?
Yes, but manage your expectations. It’s long. It’s winding. Bring Dramamine, snacks, and entertainment.
Stop at places like Garden of Eden where kids can actually get out and explore. Don’t try to hit every single stop. Pick your favorites and take your time.
We always stop for banana bread. That’s non-negotiable in my family now.
What do I pack for Haleakala?
Puffy jacket. Long pants. Beanie. Gloves. Hand warmers.
Temps at the summit are 40-45°F but wind chill makes it feel colder. Way colder.
I know it’s Hawaii. Pack winter clothes anyway or you’ll freeze and be miserable. Trust me on this. I learned the hard way.
Can you swim at the black sand beach?
Wai’anapanapa is stunning but the water can be rough with strong currents. Keep a close eye on kids if they go in.
It’s honestly better for photos and exploring the lava caves than swimming.
What’s the best luau for families?
Old Lahaina Luau. It’s the most authentic and educational. They focus on actual Hawaiian culture and history.
Book way in advance. They sell out constantly.
If it’s sold out, Te Au Moana or Grand Luau at Honua’ula are solid backups.
How much does this really cost?
For a family of four: $8,500-10,000 total including flights.
That breaks down to roughly $1,100 per day for lodging ($400), food ($200), activities ($300), car ($85), and gas ($15).
Luxury resorts and peak season will push it higher. Budget options and shoulder season can bring it lower.
It’s a lot of money. But it’s also Hawaii, so.
Start by booking that Haleakala sunrise reservation 60 days out. Then check out my complete Maui guide for way more details.
If you want personal help planning, I do one-on-one consultations where we’ll build your perfect itinerary together.
See you on Maui!
