Not Your Average Oahu Travel Guide

When daydreaming about places we wanted to travel this year, Seth and I quickly came to the conclusion that Oahu would be an idyllic getaway. Seeking a destination to recharge and relax, with plenty of opportunities for adventure, Oahu checked our boxes. We prefer a more local experience when vacationing, so started researching videos of suggested activities created by locals and browsing AirBnbs outside the buzzing city of Honolulu. Our trip included funky hidden gems and moments of pure magic.

Honolulu (population 905,000) is densely occupied, with an abundance of both chic hotels and affordable apartment rentals. We opted for a tiny house in the country and though it was a 20-30 minute drive to the North Shore and Waikiki, it was well worth the extra time. Waking up in the morning to the sound of chickens clucking, and picking fresh papayas from trees on the vibrant property was an experience unfound in the city. The lush mountains surrounding our abode provided postcard worthy views, all to be enjoyed from the bluest pool.

Hawaii is famous for it’s Spam musubi, fresh pineapples and flavorful bbq. We opted to skip the expensive luaus and created our own “food guide.” I’m a believer that traveling doesn’t always equal delicious grub because trying new places is an experiment — and that’s part of the fun! To help save you time, I’ll only include our recommended favorites.

…starting with something sweet, yet nourishing. Offering arguably the top surfing in the world but also the most heavenly banana bread I’ve ever tasted (sorry dad), the North Shore can’t be missed. Much of our favorite food was found while driving around the island. In this case, the vintage mint green Makua Banana Bread VW bus with a slew of customers holding paper packages prompted us to pull over. California native Nathan opened Makua in 2020. “To our family, Hawaii and banana bread go hand in hand. Backed by two generations of baking, we're proud to share with you our homemade banana bread, always served with Aloha!” He and his wife have been making the softest, tastiest loaves ever since.

Roadside stands and walk-up counters are treasured on “The Gathering Place” island. Within an hour of landing, we made our way to the walkup window at South Shore Grill for a taste of Honolulu’s Best Fish Tacos. There’s a reason they tout this title. The tacos are huge, fresh and full of flavor. Plus, they come with a sizable side of macaroni salad. We chatted with the owner who is extremely friendly and hospitable — a theme you’ll find throughout Hawaii. We left that first meal with smiles and remnants of coleslaw on our hands.

After unpacking and settling into our new home for the week, we deemed happy hour necessary. They say do as the locals do, so we asked our host if there were any spots nearby that he enjoyed. Waianae is home to the Pililaau Army Recreation Center (PARC) and by association, Beach House 604. He mentioned that they often offered live music — say no more! We were seated quickly with panoramic ocean views and ordered a round. The waitress set down my bright blue Coconut Girl and Seth’s beer with a smile, as the band grew more energized with each song. We watched that first Hawaiian sunset from our perch at the table, feeling like two of the luckiest people.

Haleiwa Joe’s, with it’s ocean views and seasonal menu, is our top pick for an upscale meal. I opted for the grilled salmon that was simply put, divine. Seth chose the New York Strip and describes the experience as “classy and natural.” Sitting outside on Oahu’s eminent “Seven-mile Miracle” with the grass beneath our toes while being served seasonal fare is a memory that lasted long after the pink sunset faded.

On our way to the North Shore early on in the week, we noticed a hand painted sign for coffee and smoothies. This piqued our interest, so we pulled over. There was a long line at the vivid Sunrise Shack and we observed as happy locals walked away with brilliant colored bowls of blended fruit. Topped with coconut shreds and granola chunks, we each ordered a smoothie and bullet coffees in preparation for a busy morning of surfing. We enjoyed a moment of respite flipping through a local surf magazine and sipping our beverages — coffee, coconut oil, MCT oil, grass-fed butter and vanilla.

While happily munching on peanut butter granola at one of the bright yellow picnic tables, Seth shares that he thinks the Smith Brothers are the owners. Sure enough, an article from Stab Magazine reads “Sunrise Shack was founded by Hawaiian surfers Koa Rothman, Koa Smith, and Alex Smith, and the last few seasons has seen the Shack buzzing with foot traffic due to its prime location on the strip, the local-boys-done-good draw, and their ever expanding menu of healthy morning starts.” Sunny indeed!

Apart from the grub, wave worshippers come from all over the world to surf Oahu’s renowned shores. Seth, who frequents Pleasure Point in Santa Cruz, was eager to ditch the wetsuit and experience the tropical swells commonplace for his surf heroes.

I will modestly say my surfing skills are intermediate plus and I haven’t done any travel surfing. Every year, I put myself in some challenging overhead surf with a 7’10” hybrid thruster but most of the time I get as many waves as possible on my 9’5” longboard; so coming to Oahu, I know enough to get me into trouble. To mitigate against that, my approach to Oahu was with the understanding that ‘water’ is different everywhere you go and to keep myself in comfortable spots to not crash the local scene. This was June, so the North Shore was relatively calm but there was still plenty of fun waves and thin crowds.
We stayed in Wai’anae, so I first jumped in on the west shore at Ma’ili. I chose it because it was close and a good place to get my feet wet and test out the board I bought — an 8’ foamy (the plan was to fly back with it). I didn’t want to hassle with renting and wanted to be ready to surf whenever a wave appeared along our coastal drives. I caught two lefts and was able to get comfortable with Hawaii Water. I paddled back to shore with my heart less in my throat.
Next target was the North Shore — I would take any wave on the North Shore, and again, I chose one of the first spots as you drop into the area. Laniakea was the selected break. It has great parking, beach access, and shore access to the wave. The main break is a right and looks to be more dedicated for long boarders. Within two strokes of my paddle out, I was greeted by my first sea turtle. During my time, there were on average four to five people surfing and I lost count of the waist to head high waves that I caught!
Alyssa wanted to get in on the action too, so we went to Waikiki. Obviously this beginner spot worked out. Alyssa got to her feet after a couple tries! After her arms turned to noodles, I went out further among some old time locals who were occasionally reciting mantras to summon waves. It worked for me and I caught two solid waves, one long right and one left with a nice face, and was happy to be implicitly received by the locals.
As mentioned above, I intended to fly back with my foam board but the airlines have a rule that all boards need to be bagged or properly packaged. I assumed since the board was foam that it didn’t need any extra protection and I accepted the possibilities for some dings — but I guess it is a liability for them and they don’t want to accept the risk. Even though I wouldn’t make a claim on it. But whatever, I was happy to be graced with plenty of waves on the trip and will plan better next time!

the Volcom House, a legendary spot with countless years of iconic surfing history to it’s name

We splurged on one activity during our stay and it was undoubtedly worth the money. Many companies offer ocean experiences but we chose this Waikiki Sunset Cocktail Cruise for it’s outstanding reviews. Each ticket includes appetizers and drinks, but the brilliant golden hour views of Honolulu’s skyline are what stole the show. Guests are encouraged to lay on the nets of the catamaran while turquoise waters drift swiftly beneath. If I close my eyes, I can transport back to being lightly misted by the ocean spray as we sailed further into the distance.

From surfing at Waikiki where I caught a wave that lifted me smoothly into the sky, to touring Green World Coffee, there are endless destinations to explore on this vibrant volcanic haven. We already have a running itinerary for our next trip that includes Hiking Diamond Head, more snorkeling, island hopping, residing on the North Shore and traveling during winter when the waves hit their peak. No matter when you go, I urge you to venture off the beaten path and ask locals for their preferences for a more organic island experience. As the Hawaiians say, a hui hou, until we meet again.