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The Wandering Fam Michigan Family · On Points
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Oahu with kids — The Wandering Fam

Oahu
with Kids

Pearl Harbor, the North Shore, Diamond Head & Waikiki — Hawaii’s most vibrant island

Duration 4 Days
Best Time Nov–Apr
We Paid $3,726*
Kid Rating ⭐ 5/5
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Why Oahu?

Oahu is a different Hawaii. It’s the most populated island — busier, louder, and way more to do than the other islands combined. Where Kauai makes you slow down and breathe, Oahu keeps you moving. History, hikes, surfing culture, shrimp trucks, and Waikiki Beach all on the same island. For families it’s genuinely packed with things to do, which is exactly why we did it first and saved Kauai for the decompress.

“Oahu has a completely different energy to the other islands. More city, more history, more going on. The contrast with Kauai makes doing both back-to-back one of the best two-island combinations in Hawaii.”

The honest caveat: Oahu is expensive even by Hawaii standards. Parking in Waikiki is genuinely ridiculous. Stock up at Costco on arrival day and use the free hotel breakfast as often as possible — those two habits alone save you a meaningful amount across four days.

This was the first leg of our Oahu + Kauai two-island trip in November 2025. After 4 nights here we hopped a short flight to Kauai. Full cost breakdown and flight strategy in this guide. For the Kauai leg, see our Kauai Guide →

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Our 4-Day Itinerary

Day 0 Arrival + Costco Run

Landed around 1pm at Honolulu International. First stop before even checking in: Costco. Non-negotiable in Hawaii — we stocked up on snacks, drinks, and groceries before heading to the Holiday Inn. The free breakfast at the hotel helped stretch the budget across four days. Waikiki parking is genuinely brutal at $49/day, so we left the car parked and walked or grabbed rideshares for most things within the area.

Honolulu Airport (HNL) ✈️ Costco first — always 🛒 Holiday Inn check-in 🏨 Free breakfast 🍳
Day 1 Pearl Harbor + Waikiki Evening

Pearl Harbor was first on the list. We’d forgotten to book the USS Arizona tickets in advance — rookie mistake — but luckily got walk-on tickets with only a limited wait. Book these ahead if you can, especially during busy periods. We spent about 3–4 hours going through the memorial and the free exhibits. It’s genuinely moving, and more engaging for older kids than you might expect. In the evening we walked around Waikiki, grabbed dinner, and took it easy — saving energy for the big days ahead.

Pearl Harbor ⚓ USS Arizona Memorial 🇺🇸 3–4 hours Book tickets in advance! Waikiki evening stroll 🌆
Day 2 North Shore Scenic Drive ⭐

Up early with the Guide Along app running — same app that carried us through the Road to Hana on Maui and the North Shore drive on Kauai, and just as indispensable here. The app narrates as you drive and alerts you to every stop worth making. We hit them all. Dole Plantation for the dole whip — absolutely required. Giovanni’s Shrimp Truck, the original location on the North Shore near Kahuku: we waited in the line and it was completely worth it, the garlic scampi is as good as advertised. Waimea Bay to watch the surfers work those legendary waves. The Laie Sea Arch. And Byodo-In Temple was unexpectedly one of the highlights — the kids were obsessed with feeding the koi fish in the reflecting pond and we ended up spending way longer there than planned.

Guide Along App 📱 Dole Plantation 🍍 Giovanni’s Shrimp Truck 🦐 ⭐ Waimea Bay 🌊 Laie Sea Arch Byodo-In Temple 🐟
Day 3 Pillbox Hike + Kualoa Ranch + Waikiki Beach

Early morning: Dad and Raynuv did the Pillbox Hike (Lanikai Pillbox Trail). Slightly rough in places but Raynuv absolutely loved it — fantastic 360° views the whole way up. Highly recommended if you have older kids with some hiking legs. Then we had a 1pm booking for the Jungle Expedition tour at Kualoa Ranch. On the way we stopped at the Pali Lookout — a must-stop photo moment with dramatic valley views that genuinely took our breath away. The Kualoa tour itself was a lot of fun. We drove through the jungle, spotted the various movie filming locations (Jurassic Park, Jumanji, and more), and the kids picked black plums right off the trees along the trail. I hadn’t seen those since childhood in India — we used to climb trees for them, tongues turning black for the rest of the day. Thirty years later, same feeling. In the evening we headed to Waikiki Beach with swim clothes for the kids. They played in the waves while we sat at one of the beachfront bars and watched the sun go down. A pretty perfect Oahu evening.

Pillbox Hike 🏔️ Pali Lookout 📸 — must stop Kualoa Ranch Jungle Tour 🌿 ⭐ Movie filming locations 🎬 Black plums off the trees 🫐 Waikiki Beach evening 🏖️
Day 4 Diamond Head + Fly to Kauai

Early start for Diamond Head — permits required and booked a few days in advance. It’s an easy hike, well-maintained trail, and the views of Waikiki and the ocean from the crater rim are spectacular. Great way to close out Oahu. Back at the hotel, we packed up, checked out, and caught our short inter-island flight to Kauai. Thirty minutes in the air and a completely different Hawaii was waiting for us.

Diamond Head 🌋 Book permits in advance Easy hike, great views 🌊 HNL → LIH ✈️ 30 min Kauai awaits 🌿
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Where We Stayed

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Holiday Inn Waikiki

Solid, no-frills choice that made a lot of sense for Oahu. The free breakfast across four days added up to real savings in an expensive city. Decent location for getting around Waikiki. The $49/day parking is painful but that’s Waikiki — we just left the car parked and walked or grabbed rideshares instead.

★ 118K IHG points — 4 nights

Points tip: Holiday Inn Oahu is a solid IHG redemption — good value per point in an expensive city. The free breakfast benefit adds meaningful real-world savings when you’re feeding a family of four in Waikiki for four days.

🏆 Other Points Options on Oahu

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Hyatt Regency Waikiki

Right in the heart of Waikiki, bookable with World of Hyatt points. Great location and solid family amenities. A strong redemption if you have Hyatt points to burn.

✓ Hyatt Points
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Marriott / Sheraton Waikiki

Multiple Marriott properties in Waikiki bookable with Bonvoy points. The Sheraton is right on the beach — great option if availability lines up.

✓ Marriott Bonvoy Points
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Flights & What It Cost Us

We flew Detroit (DTW) → Honolulu (HNL) on the outbound, and returned from Lihue, Kauai (LIH) → Detroit on the way home — a classic open-jaw booking that let us island hop without backtracking. The inter-island flight from Oahu to Kauai was on Southwest using a $48 credit, essentially free.

Total flights cost us just $44 out of pocket for the family — $22 each way using Avios. Here’s how we did it.

🎯 Our Flight Points Strategy

🥇 Finnair Avios (Our Winner) — American Airlines flights at 15K Avios each way, Alaska Airlines at 11K Avios each way. Way more availability than Turkish Airlines and a much simpler redemption process. A 20% Avios transfer promotion made it even better — we transferred ~21,700 points per person to get the 26K Avios needed for round-trip.
📞 Finnair booking caveat — you can’t book online. Call or chat with their agents. Search award availability on British Airways or AA.com first, then contact Finnair with your preferred flights. Slightly annoying but absolutely worth it for this value.
💡 Turkish Airlines (10K each way) — technically the best deal for United flights but availability for families during any reasonable travel window is practically non-existent. Worth checking, don’t count on it.

💰 Full Trip Cost — Oahu + Kauai

Both islands combined since it was one booking.

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Flights — $44 out of pocket

$22 DTW→HNL + $22 LIH→DTW using 60K Avios (Oahu) + 44K Avios (Kauai return). Inter-island OGG→LIH on SW $48 credit. Bags free with AA Gold status. Cash value: $1,962 + $1,646.

Saved ~$3,500 with points
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Hotels — $328 out of pocket

Holiday Inn Oahu: 118K IHG points for 4 nights (cash value ~$1,563). Grand Hyatt Kauai: 150K Hyatt points for 6 nights (cash value ~$6,187).

Saved ~$7,400 with points
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Activities — $791 out of pocket

Na Pali boat tour: $494 (Amex + Viator codes saved $160). Doggie Field Trip: $75. Kualoa Ranch: $222.

✓ Saved $160 on Na Pali
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Food & Transport — $2,563 out of pocket

Restaurants: $500. Car rentals Oahu + Kauai: $413. Gas: $150. Groceries: $400. Parking DTW: $168. Miscellaneous: $600.

✓ Free breakfast at Holiday Inn helped
We Paid (Both Islands)
$3,726
Trip Was Worth
$15,072
Saved $11,346 with points across Oahu + Kauai

Cards we used for this trip IHG, Hyatt & Avios strategy

Our Cards →

💡 Our Top Oahu Tips

Book Pearl Harbor tickets in advance. We forgot and got lucky with walk-on availability. Don’t rely on that — especially during busier periods. Book the USS Arizona memorial tickets on recreation.gov before your trip.
📱 Download Guide Along before the North Shore drive. It narrates as you drive and flags every worthwhile stop. Same app works on Road to Hana and the Kauai North Shore — worth having for any Hawaiian scenic drive.
🦐 Giovanni’s Shrimp Truck — the original North Shore location. Yes there’s a line. Yes it’s worth it. Get the garlic scampi. Don’t let anyone talk you into a different location.
🐟 Budget extra time at Byodo-In Temple. We planned 20 minutes and stayed way longer. The kids feeding the koi fish in the reflecting pond with the valley behind it is one of those unexpectedly perfect family moments.
🌋 Book Diamond Head permits a few days out. Easy hike, great views, not crowded if you go early. Book on gostateparks.org — available a few days in advance, don’t leave it to the morning of.
📸 Pali Lookout is a must-stop on the way to Kualoa. Five minutes off the highway, five minutes at the lookout, one of the best photos of the trip. Don’t drive past it.
🚗 Park the car and walk in Waikiki. At $49/day, driving everywhere adds up fast. For anything in the Waikiki area, walk or rideshare. Save the car for the North Shore drive day when you actually need it.
🍳 Use the free hotel breakfast every single morning. Feeding a family of four in Waikiki adds up quickly. The Holiday Inn’s free breakfast across four days is a meaningful saving in an expensive city.

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