6 Magical Days in Maui with a 5-Year-Old

A Perfect First Trip to Hawaii

Our easy, honest guide to making the most of paradise.

When we planned our first trip to Hawaii, we knew one thing, we wanted to experience it all. Our 5-year-old was super excited for beaches, turtles, and lots of shave ice.

The First Hello: Landing in Paradise

We stepped off the plane (San Jose, CA to Kahului) and were instantly hugged by Maui's warm, flower-scented air.

Pro Tip: Definitely rent a car (preferably a 4x4 if you're planning to do the Road to Hana).

It was 1 PM when we landed, and by 3:30 PM, we were checking into our cozy beach condo at Kaanapali. From our lanai (Hawaiian for balcony), we could see the blue ocean stretching endlessly, and turtles floating lazily right below us.

That evening, we wandered over to Whalers Village, caught our very first Maui sunset, and watched the sky turn orange and pink over Kaanapali Beach. Dinner at Leilani's was our first real taste of Aloha, fresh seafood, drinks, and a slice of hula pie.

Day 2: A Day for Sandcastles and Sea Turtles

Day two started with giggles and sandy toes, the beach was just steps from our room, and we couldn't get out there fast enough. Our 5-year-old wasted no time building sandcastles, racing waves, and collecting shells.

In the afternoon, we drove to Napili Bay, famous for snorkeling with the Hawaiian Green Sea Turtles. Lunch at the open-air Gazebo Restaurant was worth every minute of the wait, macadamia nut pancakes and ocean breezes? Yes, please.

We took a short hike across the rocks to reach the Nakalele Blowhole, and it was absolutely worth it! The ocean spray and crashing waves were such an incredible sight.

After all the exploring, we were ready to eat, and the Kaanapali Food Truck Park did not disappoint. Fresh fish tacos, the yummiest sushi rolls, garlicky noodles, fresh-squeezed sugarcane juice, and cups of sweet, juicy fruit. It was a feast for all our senses. I'm pretty sure I gained a pound (or two) right there, but every bite was so worth it.

Day 3: Snorkeling, Turtles, and Shave Ice Dreams

On day three, we started with a delicious breakfast at Island Vibes Cafe, a cozy little spot. Don't miss their amazing açaí bowls and delicious coffee. Then it was time for snorkeling at Kapalua Beach, soft white sand, crystal-clear waters, and fishes that looked like they swam straight out of a storybook.

Since we booked this trip last minute, most of the guided snorkeling tours were already sold out. But honestly, it worked out perfectly. We rented our own snorkeling gear and beach essentials from nearby rental shops. It's super affordable, and it gave us the freedom to explore at our own pace. Kapalua's calm waters were just right for beginners like us, and watching our daughter float around with her little snorkel set was a memory we'll never forget.

Later, we made our way to Ho'okipa Beach Park, where dozens of giant sea turtles were resting on the sand.

Tip: The best time to visit is in the late afternoon, when the turtles come ashore to rest.

It felt almost magical, like we had wandered into their secret gathering. We ended the day with a sweet, colorful tower of Ululani's Shave Ice (so worth the 1hr wait).

Pro Tip: Don't forget to order yours with a scoop of their famous Roselani ice cream at the bottom.

Day 4: The Adventure of the Road to Hana

The Road to Hana was something we had heard about: a winding, jungle-covered drive filled with waterfalls, hidden beaches, and endless ocean views. It definitely lived up to the hype, and the curves.

Since we weren't sure how our 5-year-old would handle the long, twisty drive, we decided to take it slow and stay overnight in Hana. (Highly recommend if you're traveling with young kids!)

We started our adventure early in the morning, snacks in hand from Maui Fruit Ninja, their fresh fruit bowls and smoothies were the perfect grab-and-go breakfast.

Our first stop was Twin Falls, where a short, easy hike led us to waterfalls perfect for splashing around and taking in the lush scenery.

Along the way, we made lots of fun little stops. We didn't do every single stop from the list below, we picked and chose what felt right for the day.

• Aunty Sandy's Banana Bread (Ke'anae Peninsula), This is a must! The warm banana bread right out of the oven is seriously unforgettable.
• Garden of Eden Arboretum, A beautiful spot to stretch your legs and take in panoramic ocean views.
• Hana Gold Cacao Plantation, Locally made, small-batch chocolate that's totally worth stopping for!
• Various Fruit Stands, Everywhere along the road! Fresh lilikoi (passionfruit), coconuts, and homemade treats.
• Waianapanapa State Park, The famous Black Sand Beach (book entry in advance!).
• Hana Lava Tube and Red Ti Botanical Garden Maze

Lunch was casual, grabbing bites and sweets at different stands, and honestly, that was part of the fun. We just stopped wherever looked good, picking up banana bread, fresh fruits, and locally sourced chocolate along the way.

By late afternoon, we made it to Hana Farms, and it felt like stepping into a tiny, happy village tucked away from the world. Live music played under the trees, the smell of wood-fired pizza filled the air, and everyone just seemed to slow down and smile. We stayed for dinner here, the pizzas were incredible, the vibe was cozy, and it was the perfect, relaxed end to a big day of exploring.

Day 5, 6 and 7: Pool Days, Luaus, and Long Goodbyes

After a night under the Hana stars, we were ready to slow things down and soak up some poolside fun in Wailea.

Our last two nights were spent at a dreamy resort in Wailea. After so much adventure, it felt wonderful to slow down, to float in the pool, walk on golden beaches, and watch the sunsets that looked like paintings.

One night, we dressed up a little and went to the Te Au Moana Luau. Under the stars, we watched dancers tell the stories of the islands, and our daughter's eyes sparkled as she clapped along.

On our final day 7, with a late flight ahead, we lingered at the resort, soaking up every last moment of Maui's magic.

Where to Stay in Maui

Kaanapali: Fun, Family-Friendly, Beachfront

Vibe: Lively resort area with great beaches, shopping, and activities.

Top Picks:

• The Westin Maui Resort and Spa ($$-$$$)
• Ka'anapali Beach Hotel ($$)
• Aston at The Whaler on Kaanapali Beach ($$)

Napili Bay: Calm, Laid-Back, Family Favorite

Vibe: Smaller resorts, calm bay perfect for snorkeling.

Top Pick:

• Napili Kai Beach Resort ($$)

Wailea: Relaxed, Upscale, Romantic

Vibe: Elegant resorts, golf courses, luxury shopping.

Top Picks:

• Wailea Beach Resort Marriott ($$-$$$)
• Grand Wailea Resort ($$$)
• Four Seasons Resort Maui at Wailea ($$$)
• Fairmont Kea Lani, Maui ($$$)
• Andaz Maui at Wailea Resort ($$$)

Hana: Remote, Natural, Peaceful

Vibe: True Hawaiian countryside, waterfalls, beaches, quiet life.

Top Pick:

• Hana-Maui Resort ($$-$$$)
• Vacation Rentals: Various options ranging from cozy cottages to luxurious estates.

Foodie Favorites You Can't Miss

If you ever find yourself in Maui (and you should), don't miss:

• Mama's Fish House, Legendary seafood and stunning ocean views.
• Duke's Beach House, For fish tacos and that famous Hula Pie.
• Monkeypod Kitchen, The best Mai Tais.
• Merriman's Kapalua, A sunset dinner you'll dream about.
• Hula Grill, Toes-in-the-sand dining at Whalers Village.
• Leilani's on the Beach, Fresh seafood and Hula Pie right on the beach. Great for sunset dinners!
• Food trucks, Kaanapali Food Truck Park is a must.
• Leoda's Kitchen and Pie Shop, Banana cream pie heaven.
• Sugar Beach Bake Shop, Fresh malasadas, homemade pies, and delicious coffee.
• Maui Thai Bistro
• Coconut's Fish Cafe
• Hana Farms Pizza, Fresh from the oven in a jungle garden.

Things We Wish We Booked Early

Since our trip was pretty last minute, a lot of popular activities were already fully booked. If we had planned a little earlier, here are the experiences we definitely wouldn't have missed:

• Trilogy Sunset Cruise, Dreamy catamaran tours from Kaanapali.
• Molokini Snorkel Tour, Clear water and coral reefs.
• Sunrise at Haleakala Crater

What to Pack for Maui (Especially with a Little One!)

Packing for Maui is all about staying comfortable, sun-safe, and ready for adventure. Here's what we packed:

• Lightweight clothes (shorts, tank tops, sundresses)
• Swimsuits (you'll live in them)
• Beach cover-ups
• Flip-flops or sandals
• Sneakers or water shoes (for hikes and rocky beaches)
• Light jacket
• Sunhat and sunglasses
• Reef-safe sunscreen (Protects the ocean and is required by law in Hawaii)
• Snorkel gear (or plan to rent locally)
• Beach towels or quick-dry towels
• Waterproof phone case
• Dry bag (for beach days or the Road to Hana)
• Foldable beach bag for carrying snacks, towels, toys
• Basic first-aid kit (band-aids, wipes, motion sickness bands if driving Hana)
• Portable phone charger (great for long days out)
• Ziplock bags (for wet swimsuits or sandy shoes)

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We didn't just bring home souvenirs but we carried a little piece of Maui with us. The fresh leis we wore on the island now hang in our home, a simple, sweet reminder of a trip where we slowed down, laughed more, and soaked in every moment.

Aloha, Maui. We'll be back for more magic.