Exploring North Shore, Oahu

When we started planning 50 in 5, Brandon and I knew we wanted to bookend the bigger, more expensive trips (Alaska and Hawaii) in the first and last years. We visited Hawaii over Brandon’s 30th birthday in February 2018—a dream vacation that I sometimes still can’t believe actually happened. I’m going to write about the trip in three parts. Today: planning, travel, and exploring North Shore, Oahu.

North Shore, Oahu

Planning a week in Hawaii

The Hawaiian Islands are nearly 5,000 miles away from our home in North Carolina. With lengthy travel days, it didn’t seem worth it to visit Hawaii for less than one week. Brandon and I earn less than 3 weeks of vacation time per year, so choosing to spend a third of it in one place is a major consideration. We need to visit an average of 10 states per year to meet our 50 in 5 goal. Going to Hawaii meant that we should, in theory, visit nine additional states in two weeks this year. Yikes.

Distance also impacted our budget, because flights from the East Coast to Hawaii are notoriously expensive. We knew that travel and accommodations would be the largest expense, and as I researched I became discouraged until I had a great idea: invite friends! One of our goals of 50 and 5 is to include friends and family in our travels. We stayed with friends in California, and flew to Colorado last year with our friend, Alyssa. Brandon invited his brothers to experience Hawaii with us, and we were thrilled that his brother, Josh, and sister-in-law, Chelsea, were eager to vacation with us. We split the cost of the Airbnb, rental car, and groceries during the week.

Travel day and home base

Our flight departed from Raleigh at 7:35 am, and we had a short layover in Dallas before continuing to Honolulu. We arrived at 3:15 pm local time (8:15 pm at home) and scurried over to Hertz to pick up our rental for the week. From there, we had a 40 minute drive to our Airbnb on the North Shore.

We opted to visit only the island of Oahu on this trip. I knew early on that I wanted to stay on the North Shore, away from the bulk of the tourists in Honolulu and Waikiki. You can drive from one end of Oahu to the other in almost exactly an hour, so  I didn’t feel like we were too removed from anything we wanted to do. I found a few different Airbnb listings and sent them to our group to pick a favorite. We landed on an affordable place in a quiet neighborhood, with a short walk to the beach.

North Shore Oahu Airbnb

North Shore Oahu Airbnb
I took these photos of the Airbnb on our first morning in Hawaii. I had been awake since around 5:15 am!

string lights

Honolulu rental car

One huge perk of our Airbnb is that it had a full kitchen, which meant eating all of our breakfasts and some lunches and dinners at home. Some people don’t want to cook while on vacation, but that never bothers me. It saved us a lot of money, too! We enjoyed having an outdoor area to relax, along with an outdoor shower. We also had a very friendly rooster around who made sure we were awake before the sun. I sat outside every morning attempting to meditate while listening to him. 😉

eggs in a frame
In addition to lots of eggs and bacon, we ate fresh pineapple every. single. day.

North Shore, Oahu

We were all feeling a little #hangry when we arrived, so after dropping off our luggage at the Airbnb, we hurried to nearby Haleiwa to grab dinner and then to Pūpūkea to pick up some groceries. I was surprised by how busy the shops and restaurants in Haleiwa were. The Volcom Pipe Pro is held on the North Shore every February, which brings an influx of visitors to that part of the island. We timed the trip well, because we had the opportunity to spend part of Brandon’s birthday watching pro surfers compete with 18-20 ft. waves!

Haleiwa, Hawaii

Volcom Pipe Pro

Volcom Pipe Pro

Several times during the week we drove along the North Shore exploring, without any real agenda. We discovered several good food trucks and fruit stands, and a place to snorkel (more on that in my third Hawaii post). The locals we met were kind and extremely laid back. As we stood in line at the crowded grocery store on Saturday night, I wondered if they are ever annoyed by the number of mainlanders who vacation in their small town (population < 4,000).

Oahu fruit stand

Coconut drinks

Oahu fruit stand

Giovanni's Shrimp Truck

Giovanni's Shrimp Truck
Why haven’t we moved to Hawaii to eat this shrimp every day?

surf boards


Matsumoto Shave Ice

surf boards

I really loved our neighborhood, too, though we didn’t spend a whole lot of time there. Our beach access was uncrowded and gave way to beautiful views of the Pacific Ocean. The green cliffs opposite the neighborhood were beautiful, and I spent a lot of the week commenting on whether or not I should be looking at the beach or the mountains, as they were equally stunning. My favorite souvenir from the trip is a print I picked up from Polu Gallery in Haleiwa. In bright green and blue, it depicts the balance between Hawaii’s mountains and oceans. We hung it prominently in our living room, and it reminds me of our trip every time I walk by.

Kaena Point
Josh and Chelsea hiked at Kaena Point State Park near our Airbnb – look at that view! / Photo: Chelsea Callaway

Pink flowers

Aloha sign


banyan tree
We walked through (yes, through) this banyan tree at Turtle Bay Resort.
"Lost" filming location
They filmed the plane crash scene from one of our favorite shows, “Lost,” on this beach. We also spotted a YMCA camp that served as home base for the Dharma Initiative.

North Shore, Oahu neighborhood

North Shore favorites

Kaena Point State Park was an awesome spot. We walked around for a bit one evening, but Josh and Chelsea returned and did an entire hike. We also spent a fair amount of time at Pūpūkea Beach Park. We ate dinner at Haleiwa Beach House on Brandon’s birthday and also stopped at Giovanni’s Shrimp Truck, North Shore Tacos, Matsumoto Shave Ice, and Haleiwa Joe’s during the week.

My one regret is that we didn’t see any sea turtles while we were in Hawaii. I’ve heard that Laniakea Beach is a great spot to view them. We stopped there on our first night, but didn’t realize it was a place for prime turtle viewing. We didn’t see any. Guess we’ll have to go back!

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