Oahu 101: A Waikiki Week with Everyone

Even a room-without-a-view leads to the perfect multigenerational Hawaii vacation…

By Amy Jordan Jones

When my stepdad suggested we surprise my mom with a family trip to Hawaii, I was tempted. When he offered up a week in one of my parents’ [many] timeshares, I was sold. And when my husband suggested that we extend the multi-generational family trip by a couple of days with just our family of five?  Well, frankly, I felt like I won the lottery.

After a lifetime in California we were finally heading to Hawaii with the kids: First to Oahu with the extended family for a week and then to Kauai for an extra five days at the end.

At the time, our kids were 12, 10 and 5. While we have always taken family trips, this one felt different. Maybe it was the distance? Maybe it was the fact that we were traveling as a group with our extended family? Maybe it was that it was the kids’ first tropical vacation? Whatever it was, the excitement was palpable.

After we #FINALLY [see “The Journey” below] made it to Oahu, we were more than ready to get into the aloha state of mind. My parents’ timeshare was right in downtown Waikiki, across the street from the beach. We had a two-bedroom condo. My brother, sister-in-law, and their three kids got the unit with a better view. I wasn’t bitter [except I was] but I was willing to put up with the injustice in return for the free babysitting – and the chance to give us a family trip we’d never forget.


And Honolulu delivered. Oahu has got everything everyone needs for a perfect multigenerational trip:

The Best of Oahu for Families

  • Beauty – It’s Hawaii!
  • Accessibility- There are restaurants, stores, access to surf lessons, parasailing, snorkel trips, sunset cruises etc. minutes away by walking or driving. One day I needed rash guards for my kids and I was able to buy them right across the street.
  • Pearl Harbor – A truly one-of-a-kind experience to be able to see history come to life
  • North Shore – A place to get more of that “island feel” on Oahu
  • Something for Everyone – There is always something for us all to do. If we went to the North Shore, my parents laid out on the beach. When we went to Pearl Harbor, the little kids could stay with grandparents. Everyone wins!
  • Parent Nights Out – Because grandparents are awesome, we parents could head out to any number of fun restaurants/bars in Waikiki while they babysat the kids.
  • Waikiki Beach – Unique in the islands as a happening, bustling spot with a wide white sand beach, palms everywhere, and a strand lined with fun hotel lounges to wander past and peoplewatch.


Sure, I could eat at a Cheesecake Factory and shop at Macy’s within a few miles from my house in California, too, but the memories of our island time together as a family on Oahu will last a lifetime. Thanks Nana & Grandpa Jim!


The ROAM Report
Waikiki, Oahu, Hawaii

Travelers: The Jones Family (parents and three kids, 12, 10, 7) plus grandparents, aunt, uncles, and three cousins
Dates: August 2017
Itinerary: 1 week in Waikiki with day trips around Oahu
Budget: Activities and food are downright expensive. Budget about $75/per person per day for the week for everything aside from flights, lodging and car rental.

The Good Stuff

Tips for Pearl Harbor with Kids

Our day in Pearl Harbor was one of the best experiences we had in Oahu. We booked the Aloha Pearl Harbor Tour and it was fabulous. History truly came to life for our two boys.

Our group picked us up at about 5am and we were back at our condo by 1pm after the bus driver gave us a little tour around Honolulu, which was really interesting. Here’s a few important tips about Pearl Harbor:

  • Older Kids Better I am glad that we left the younger kids (under 6) back at the hotel with Nana. They would not have enjoyed it and their unhappiness with such a long “boring” day would have detracted from our experience. That said, my little brother really enjoyed himself.
  • Book Ahead It is important to book far ahead of your trip to be sure you can get your group in. And if you don’t come early or with a group, you are forced to wait in line and might not even make it in which would be a terrible waste of a day on the island.
  • Go your First Day We were glad we visited Pearl Harbor on our second day in Oahu when we weren’t yet on Hawaii time. When you take a tour, they pick you up super early so you can get there to avoid the crowds. That meant getting up at 4:30am felt more like getting up at 7:30am in California.The 5am departure also meant the tour didn’t take up an entire day which was ideal.

Cliff Jumping on the North Shore

Our trip to North Shore quickly became the other highlight of Oahu. Away from the busy streets of Waikiki, this was the first time I really felt like we got to experience the tropical Hawaiian paradise. The vibe was way more mellow, the beach was obviously a local hotspot, and the cliff jumping was out of this world.

There was a huge 30-foot jump from the rocks with posted signs “Danger: Stay Away” but this advice was ignored. As soon as my boys and nephew saw people flipping and launching themselves off the cliff, they were anxious to give it a try. I was nervous at first but they handled it like champs.

By the end of the day, even I decided that it was “now or never” and began the trek to the top. The jump had looked imposing from the safety of the beach but standing up there looking down at the water, it seemed nearly impossible. However petrified, I refused to do the “walk of shame” back to the bottom, and with a pep talk from some friendly locals, finally gained the courage to take the plunge. The applause from the people both on the rock and the beach was both endearing and humiliating.


Must-Do Luau for Families

What Hawaii trip would be complete without some roast pig, mai tais and hula? We went to the Chief’s Luau and found it the perfect multigenerational event: Lots to do for the kids, an entertaining show, great food and drinks, buses picked up/dropped off our group, all very fun and very organized. It was expensive (about $100/pp plus transport) but we felt we got our money’s worth.


Turtle Canyon Snorkel Sail

My brother Zack picked a 2.5-hour snorkel tour on the Holokai as his choice for a group activity and he STILL brags that he “nailed” it. And I must say that even though he basically walked 20 feet down the beach and found this company, it was AMAZING. The boat and crew were awesome, the equipment was provided, and they helped us with everything – oh, and the snorkeling was great too. It was truly fun for everyone: my 3-year-old niece who wasn’t into the ocean was super happy staying topside on the boat, my 5-year-old daughter who felt totally comfortable jumping off the boat, the boys who were thrilled to see the sea turtles, my mom who was happy having everyone together, and we parents who were happy about the “Holokai Hooch” – soooo yummy! The Holokai also offers other types of trips, like a sunset cruise. This trip got the need-to-snorkel out of our system so we never made it to Hanauma Bay or the many other places to snorkel around Oahu.


Surf Lessons for Kids on Waikiki

Nana bought a private group surf lesson for the three older boys, my brother and my husband as birthday gifts prior to the trip – such a great idea! Big Wave Dave gave great lessons – they all “got up” right away.


Waimea Falls: The Perfect Multigenerational Day Trip on Oahu

The grandparents, parents and kids all loved Waimea Valley and Botanical Gardens. It was beautiful and an easy walk for everyone to reach Waimea Falls.


Great Family Restaurants in Waikiki

Though not cheap, Waikiki was a great place for tons of family-friendly dinners. We also managed to have Nana babysit so the parents could head out at night. We liked Tiki’s Grill and Duke’s Hawaii. Both were kind of touristy but close by and we thought they were worth the hype.


Best Group/Family Photographer in Oahu

We knew we needed to preserve this trip in time and what better way than to hire a professional photographer to capture the fun. I reserved Krystal Kirkland Photography and absolutely loved her.


Amy Jordan Jones – December 2018

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