There was a time when holidays consisted mainly of trips to Hawaii and California when our twins were small. These are both very popular vacation destinations for Seattle families and both have nonstop flights. We still go to California often and Hawaii Island the past couple years for multigenerational trips. Last year we realized we hadn’t been to Oahu since the kids were very small. We had 4 nights for Memorial Day weekend and for us it’s always difficult to figure out if we want to stay in the same place for the duration of our trip or if we want to break it into more places so we can see more (we don’t tend to stay in one place longer than 3 days). On a recent short trip to Nassau we broke our 4 night trip into two and two. On a trip to London for Thanksgiving we did three nights in the same hotel. So on this Oahu trip we decided to do two nights at the Outrigger Reef Beach Resort and two nights in an Airbnb on the North Shore and we love the way it turned out. It balanced a bit of the city feel of Waikiki with a bit more remoteness and calm of the North Shore and both were beach front so we still felt like we got enough sand in our shoes. And the Outrigger Reef ended up being a really great choice with teenagers in tow.
Outrigger Reef on the beach
I had trouble deciding between the Outrigger Reef Beach Resort and the Outrigger Waikiki Beach Resort and originally had four nights booked at the Outrigger Waikiki Beach Resort (it had a deal) but ended up canceling and going with two nights at the Outrigger Reef for nostalgia. We stayed at the Outrigger Reef when the guys were about 3 years old and I think at least another time too. It’s changed a bit-there’s no longer the Shorebird restaurant that we’ve been going to for years but we enjoyed the new to us restaurant at the hotel, the MonkeyPod Kitchen. Manoa DNA, the band we first listened to together here is no longer a band too, but we enjoyed live music with dinner here one night on this trip as well.
When I looked at the old blog post, I remembered us boogie boarding around our hotel room watching surfers outside because the boys were so tiny. This time our teens signed up for a surfer class one morning (there was literally a surfing school right under our balcony- Gone Surfing Hawaii) and then the hubs joined them for surfing the next day as well. (these guys have all taken lessons together before too in Maui last year. One of these days I need to try it with them!) We booked an ocean front room at this resort so we could look out at the water.
Because teenagers sleep in, we were able to walk to coffee shops in the morning hours. Honolulu Coffee company had a huge line when we got there and we enjoyed their delicious coffee. It was easy to grab fresh musubis from nearby cafes like Musubi Cafe Yasume. And we kept walking by Henry’s Place and it was always lined up and it turns out it was selling a kind of delicious homemade sorbet/ice cream. One morning we also picked up Leonard’s Malasadas and ate them on our balcony. We walked to a food hall that wasn’t here the last time we visited. On our way to the North Shore we stopped at a place called the Kansai Yamoto Cafe and I will dream about their strawberry mochi for a while.
Kahuku beach house Tiny home rental on Oahu’s North Shore
The last review I can find for the tiny home we rented was at the end of December 2024 and sadly I think this rental near Mālaekahana Beach is now gone (I’ll keep checking). The guys couldn’t get over the outdoor shower/bathroom and the beach was literally out our door. You might try this rental if you want a similar experience. You can also find rentals near Turtle Bay Resort and the resort itself is lovely but we haven’t been there in years. It’s nice to be near to places like Ted’s Bakery and Shark’s Cove and Matsumoto’s Shave Ice (At Matsumoto’s they even had a shave ice where you can eat the bowl!). It was also really near Kahuku Farms and I wanted to do a farm tour but we didn’t have enough time. Where we stayed the water was a little rough to swim in but we had a lot of water on this trip. We enjoyed pancakes on a beach practically to ourselves. I am not always a fan of what Airbnb type rentals can do to a community (we have them in Seattle and near our cabin too) but I do appreciate when we can imagine what it might be like to live in an area without feeling like a total visitor. This was such a beautiful way to stay on Oahu’s North Shore for a little while and none of us wanted to leave.
Have you ever been to Oahu? Do you have a favorite hotel or home rental?
Terumi Pong is a Seattle-based family travel writer and mom of twin teenage boys. She loves coffee and pastries, shopping local and looking for greener ways to live. She is also known as Scout’s mom (Scout is a 5ish pound little black yorkie-poo)
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