*Last updated on October 11th, 2017 at 03:31 pm
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We just got back from our second family trip to Oahu and my third trip overall. The first time we had to figure out how to navigate Hawaii with a baby but this time we had 2 little preschoolers to deal with! We made very few plans, but in hindsight, a little more structure would have been nice. At the very least, it would have cut back on time we spent deciding what to do!
The home-base for this itinerary is Haleiwa on the North Shore but you can adjust it to meet your needs. We explored most of the island and didn’t hesitate to drive because nothing was further than an hour away! One advantage of staying on an island!
We stayed with family this trip, so we tended to eat a lot of meals back at the house. (Thanks for cooking Auntie! 😊) Even if you’re staying in a hotel without a kitchen, you can still save a lot of money by eating cereal and sandwiches for breakfast and lunch. Restaurants in Hawaii are expensive and eating out is just not fun for the kids, so easy low-maintenance meals are perfect!
5 Days on Oahu Itinerary
Day 0: Arrive in Honolulu
Grab your luggage, hop in a rental car (or bus, shuttle, taxi, etc.), and check-in to your accommodations. Unpack and make sure to toss all of your beach gear in the trunk of the car. When you head to the beach, make sure it’s the closest one. There’s no reason to spend extra time in the car today.
Make sure everyone drinks plenty of water and spends as much time as possible outside. Staying hydrated and spending plenty of time in the natural light will help combat jet lag.
We spent the entire first day hanging out with our family. We could probably have squeezed in a quick trip to the beach, but it was good to catch up!
Day 1: First Full Day on Oahu
We took advantage of our jet lag and hit the beach early! We drove to the east side of the island to watch the sunrise and then eat breakfast on the beach. We purchased compostable spoons, bowls, and some special vacation cereal and kept it in the trunk of our car. On any given morning we just had to grab milk from any grocery store or gas station and we were ready for breakfast on the beach!
From where we were staying on the North Shore, Hukilau Beach was convenient and a wonderful place to watch the sunrise. This was also our favorite sunrise beach back in 2014! There is a Foodland 2 minutes down the road, so you’ll be all set for breakfast.
After the sun comes up, you can still enjoy the beach! Just remember to protect yourself from the sun. On our first morning we set up the tent and I read while the kids and Chris made sand castles. The highlight of K’s morning was watching a couple of labradors splashing in the waves.
My children still take afternoon naps and by 11 am, the whole family was ready for a siesta. We headed back to the house for sandwiches and snoozes.
I wish we had stopped by Laniakea Beach to look for sea turtles. We only ended up seeing one on this trip (whereas we saw dozens back in 2014) so I wish we’d made a point of looking for them earlier in the week.
After your nap, head to Waimea Falls to hike and swim. The hike is paved and less than a mile, so don’t let it scare you off! Taking the kids swimming at a waterfall is really a special experience.
Day 2: Exploring Oahu
We had reservations for the Paradise Cove Luau on Day 2, so we planned the entire day around that.
After breakfast, we drove down to Ulua Lagoon #4 to enjoy some time at the beach. There is free parking, but the line for it was crazy, so we used the $10 all-day parking lot next to the marina. If you want the free parking, get there early. It also happened to be a holiday weekend when we were there, so there may have been more locals than usual.
The beach itself has white sand and wasn’t too crowded. Maybe it was because everyone was in the water or maybe people were choosing to leave their stuff on the perfectly manicured lawn. We set up our tent, but someone from the resort came and told us there were no tents allowed. Whether or not he had the authority to enforce that on a public beach was a little unclear, but we took it down.
The water was more crowded, but we still had plenty of space to swim. The lagoon does get quite deep pretty quickly, so be prepared with floats for your non-swimmers.
After a morning at the beach, we had a delicious lunch at Longboards in the Marriot. We sat outside and had views of Lagoon #3 while we ate. Lunch was delicious and it was also cool to see all the landscaping and water features that were part of the Marriot. I can definitely see the appeal of a place like that, even though all the pools seemed quite crowded.
We spent naptime on my Aunt and Uncle’s boat in the marina. I read on the deck while the rest of the family snoozed in the cabin.
We finally had to wake the children up to take them to the Luau. We should have gone an hour earlier and we ended up missing some of the activities, but the children were tired and needed to rest. The luau itself was great fun and I definitely recommend attending a luau if you have young children. Even though they are a bit touristy, they do convey some of the history and culture of the Pacific Islands. This was the first trip where we taught the kids a bit about Hawaii before we came and the luau really helped reinforce what they had learned.
Day 3: Adventures on Oahu Continue
We greeted the day with another low-key morning at the beach. My children never get tired of building sand castles or playing in the waves. Hawaii is definitely the perfect place for that and you could easily spend a full week doing nothing but exploring the beaches.
For lunch, we drove into Honolulu for Dim Sum. If you are coming from California this may not be as exciting since there is lots of excellent Dim Sum in California, but when we came from NC in 2014, this was a trip highlight! There are large Chinese and Japanese communities in Hawaii and the excellent food reflects that!
After lunch, we stopped at Pearl Harbor. We didn’t take any of the ship tours, but we walked around and looked at the monuments. It was a short trip since the children were uninterested, but it’s an important part of history and I’m glad we went.
Chris dropped me off to get my hair cut in Pearl City while he took the kids to a playground. At home, I always feel like there are too many things going on to take the time to get my hair done, knocking it out on vacation felt like a smart move! If you don’t need a haircut, maybe convince your spouse to let you have an hour at the spa. 😉
Day 4: Oahu Windward Side
We started Day 4 with a special Disney Character Breakfast at Aulani. It was the week of HJ’s birthday and it was a fantastic way to add a little *extra special* to our vacation.
Since we were already all the way in Ko Olina, we decided to spend the day making our way to the North Shore while exploring the windward side of the island.
We cut straight through the island to start the tour at Lanikai Beach, but if we hadn’t done the Disney breakfast we would have started the day at Haunoma Bay.
Lanikai was our favorite beach back in 2014 and it didn’t disappoint this time either! The sea was calm, the water was clear, and the scenery was perfect. Chris went snorkeling and saw an eel and a sea turtle. He said there weren’t quite as many fish as at Shark’s Cove but there was more diversity and the water was clearer.
On this trip, all our snorkeling was just Chris going solo while I watched the kids, but we ran into someone with a full face snorkel mask for kids and she let HJ try it out. The concept of staying underwater and continuing to breath was new for HJ but I’m sure she could have mastered it with more practice. I’m definitely going to look into getting one of these for our next tropical trip.
Chris did swim with HJ on his back and tried to point out fish when he saw them. She had goggles on, but she always told Chris she couldn’t see them. When they came back to shore she told me she saw hundreds of fish. A mystery.
When we were all beached out we loaded up the car and started the longish drive up the east coast. The highway stayed right next to the water most of the trip and there are some incredible views. It’s truly a can’t-miss drive.
We stopped once for shave ice and again for fresh coconuts, but mostly drove without stopping until we grabbed an early dinner at Fumi’s. By this point in the trip, I was drooling for some shrimp and we ended up choosing Fumi’s at the recommendation of my Aunt and Uncle.
Most of the shrimp trucks are cash-only and we were down to $24 cash, but it turned out to be plenty for all of us. We got 1 order of garlic shrimp, 4 corns, and a couple bottles of water. If we had been there at dinner time proper we would have needed more, but for a 4 pm dinner it worked out great! HJ usually doesn’t eat shrimp but she gobbled up 3 of them!
After dinner, we headed to Shark’s Cove to let Chris snorkel some more!
On the North Shore, Shark’s Cove is the place for snorkeling. Chris saw tons of fish but found the water slightly foggy. You will definitely need Keens or something similar for walking over the rocks to get to the water. There is also no sandy beach surrounding Shark’s Cove, but you can find a sheltered sandy area just about 100 yards to the North. The kids and I played there while Chris was snorkeling.
Oh, and if “Shark’s Cove” sounds like a terrible place for snorkeling? It gets its name from the rock formations that look like a shark’s mouth. Quite a few people were snorkeling when Chris was there and no one got eaten. 😊
Day 5: Wrap Up Oahu
Day 5 is the day I really think we would have benefited from having a plan. So, instead of telling you what we did (which involved a lot of aimless driving, showing up at beaches with no beach, bickering, etc.) I am going to tell you what you should do!
Wake up early and drive out to Makua Beach. It’s a bit of a drive, but it’s supposed to be a beautiful and uncrowded beach where you can often see dolphins or whales. Pack your lunch because this area is not built up and there won’t be lunch options.
After playing on the beach (or maybe before?) take the hike to Ka’ena Point. Remember to bring the kid carriers and comfy walking shoes.
We spent our last night at Haleiwa Joe’s with my Aunt and Uncle. It was such a wonderful trip and we are so lucky to have family that live in this beautiful place!
Day 6: Pack up and Aloha!
My Aunt made us Loco Moco for breakfast and we were able to spend a few minutes together before we headed back to the airport. We also had time to grab a last-minute gift from the Black Pearl Source! Other than my magnets, jewelry makes the best souvenirs!
The airport was easy to navigate and we found ourselves at the gate with plenty of time to spare. Aloha Hawaii! We can’t wait to come back! ❤️
I hope our Oahu itinerary is helpful as you plan your own trip! Having a plan is great, but keep it loose and allow for spontaneity! Hawaii is a great place to just kick back and relax!