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Hawaii With Kids

Hawaii with kids — The Wandering Fam

Hawaii
with Kids

Four islands, two trips, one family — our complete Hawaii guides

Islands 4 Islands
Duration 7–14 Days
Best Time May & Sept
👨‍👩‍👦‍👦 The Wandering Fam Verdict
Kids Loved It
10/10
★ ★ ★ ★ ★
Parents Loved It
10/10
★ ★ ★ ★ ★

Why: Hawaii is the rare destination where every age group is genuinely engaged — toddlers chasing waves, kids snorkeling with turtles, parents soaking in volcano sunsets. Across four islands and two trips, we never had a “this isn’t working for the kids” moment, and we never had a “I wish we’d gone somewhere else” moment either. It’s the only destination we’ve returned to and would happily return to again.

✓ Best For
Beach families, snorkelers, adventure seekers, points-hotel hackers
✗ Skip If
You hate long flights, prefer city vacations, or have a tight cash budget in peak season
🚗 Need a Car?
Yes on Big Island, Maui & Kauai. Optional on Oahu if staying in Waikiki
↺ Would We Return?
Already did — and we’d go back to Big Island, Kauai, or Maui in a heartbeat

Hawaii is one of those places that genuinely lives up to the hype — and we’ve now done all four major islands with the kids. Golden beaches, active volcanoes, lush rainforests, and some of the best snorkeling in the world. We keep coming back.

“Plan for at least a week even if you’re only doing one island. The flights are long from mainland USA, especially the East Coast — make it worth it.”

Between two trips we’ve done Big Island, Maui, Oahu, and Kauai — and used points to save over $22,000 across both. Each island has a completely different personality. None of them disappointed.

Sweet Spot
April–May &
Sept–Oct
Also Great
Mid-Nov to
Early Dec
Avoid
Summer & Spring Break
Packed & pricey
Main Airports
OGG · KOA
HNL · LIH

Hawaii With Kids: Our Top Pick From Each Island

Each Hawaiian island has its own signature experience — the one moment we still talk about months later. Here’s the standout from each.

🌄
Big Island
Sunset at Mauna Kea
A short hike to the mountaintop and a sunset above the clouds that took our breath away
🛣️
Maui
Road to Hana
Waterfalls, bamboo forests & black sand beaches along Maui’s most legendary drive
Oahu
Pearl Harbor
Toured the USS Arizona Memorial — the most moving historical site we’ve taken the kids to
🏝️
Kauai
Na Pali Coast
Boat tour past Kauai’s emerald cliffs — only seeable by sea, sky, or a serious hike
✈️

Our Two Hawaii Family Trips: Big Island, Maui, Oahu & Kauai

We’ve done Hawaii twice as a family — each time covering two islands in one trip. Here’s the quick summary of both, including what we spent and what the trips were actually worth.

March 2024
Big Island + Maui 🌋🌺
13 days — volcanoes, stargazing, Road to Hana & Trilogy snorkeling
We Paid
$5,221
Trip Value
$15,981
Saved
$10,663

Flights on 160K Amex points. Holiday Inn Big Island on 120K IHG points. Hyatt Regency Maui on 175K Hyatt points (5 nights, resort fee waived). Maui Ocean Center was free with our ASTC membership.

November 2025
Oahu + Kauai 🏄🌿
12 Days — Waikiki, Pearl Harbor, Na Pali Coast & Waimea Canyon
We Paid
$3,726
Trip Value
$15,072
Saved
$11,346

Flights on 60K Avios (Oahu) + 44K Avios (Kauai return). Holiday Inn Oahu on 118K IHG points. Grand Hyatt Kauai on 150K Hyatt points (6 nights). Luggage free with AA Gold status. Na Pali boat tour partially covered by Amex + Viator codes.

Both Hawaii Trips Combined
We Paid
$8,947
Trip Value
$31,053
We Saved
$22,106
Points & Miles used  ·  Amex MR · IHG · Hyatt · Avios
🏝️

Which Hawaiian Island Is Best for Families?

Each island has a completely different personality. Here’s our honest take on which one fits which kind of family — and which one we’d pick first.

The Quick Match — Which Island Fits Your Family?
🎢 Lots of activities — beaches, farm tours, ATVs, Disney’s Aulani
→ Oahu
🔭 Nature, stargazing, manta rays & deep snorkeling
→ Big Island
🏞️ Canyons, hiking & the Na Pali coast
→ Kauai
⚖️ A mix of nature and fun family activities
→ Maui
🌋

Big Island

Active volcanoes, Mauna Kea stargazing & Fairwinds snorkeling. Hawaii’s wildest and most diverse island.

6–7 Days May & Sept
Read Guide →
🌿

Kauai

Na Pali Coast, Waimea Canyon & the lushest scenery in all of Hawaii. The Garden Isle.

5–7 Days
Read Guide →
🌺

Maui

Road to Hana, Trilogy Lanai snorkeling, Haleakalā summit & the best sunsets in Hawaii. The best balance of nature and family-friendly fun.

5–7 Days May & Sept
Read Guide →
🏄

Oahu

Waikiki, Pearl Harbor, the North Shore & the most kid-friendly beaches in the state.

3–5 Days
Read Guide →
Our Personal Ranking
We’re nature people — here’s our honest order
After doing all four islands, we’d rank them differently than most travel sites. Take it for what it is — one family’s honest take.
1
🌋 Big Island
The most variety. Volcanoes, Mauna Kea sunsets, amazing snorkeling — felt like four trips in one.
2
🌿 Kauai
The most dramatic scenery in Hawaii. Na Pali Coast and Waimea Canyon are unforgettable.
3
🌺 Maui
Best balance for families — enough nature to feel adventurous, enough comfort to feel like a vacation.
4
🏄 Oahu
Great for activities and history, but felt more developed and city-like compared to the others.
💡 One thing we’d add: The resort matters more than you’d expect. After a long day of adventure, having a great pool, beach access, or kids’ club made a real difference — for everyone’s recovery, and the kids’ memories. Don’t underestimate where you stay.

💡 Hawaii With Kids: 6 Tips We Wish We Knew Before Going

✈️ Island hop if you can. Inter-island flights are short (~30 min) and inexpensive. Each island has a completely different personality — doing two in one trip is very doable and worth it.
🛒 Costco on Day 1 — every island, every time. Every island has one. Stock up on snacks, sunscreen, drinks, and food before hitting the resort area where prices are brutal.
🏨 Hyatt, IHG, and Marriott all have great Hawaii redemptions. Hyatt Regency Maui, Grand Hyatt Kauai, Waikoloa Marriott, Holiday Inn Big Island and Oahu — we’ve used all of them. Book 4+ months out.
🤿 Book snorkel tours before you land. The best tours — Trilogy on Maui, Fairwinds on Big Island, Na Pali boat tours on Kauai — sell out weeks in advance. Lock these in as soon as dates are confirmed.
📅 One week minimum. The flights are long from the mainland. Don’t rush it — give yourself at least 7 nights to actually enjoy it rather than just recover from the jet lag.

How we fund Hawaii with points See the cards behind both trips

Our Cards →

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