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The Wandering Fam Michigan Family · On Points
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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
Kid Rating ⭐ 5/5

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 the Midwest — 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
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Our Hawaii Trips

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 🏄🌿
2 weeks — 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 Trips — We Paid
$8,947
Combined Trip Value
$31,053
Saved $22,009 with points across both Hawaii trips
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Island Guides

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Maui

Road to Hana, Trilogy Lanai snorkeling, Haleakalā summit & the best sunsets in Hawaii. Our favorite island for families.

5–7 Days May & Sept
Read Guide →
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Big Island

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

6–7 Days May & Sept
Read Guide →
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Oahu

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

5–7 Days
Coming Soon
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Kauai

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

6–7 Days
Coming Soon

💡 Hawaii Tips for Families

✈️ 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.
🎨 ASTC membership saves real money. We got into Maui Ocean Center free (normally $138). If you have kids and visit museums or aquariums, an ASTC-affiliated membership pays for itself quickly.
📅 One week minimum per island. 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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