An Average East Coast Surfer's Guide to Oahu
Last summer, we placed a winning bid on a “House on Pipeline” auction package at the annual Surfrider Foundation charity event in Montauk, with the intention of traveling there over the winter when Pipeline is “firing.” But unsurprisingly, the house was already booked from October to April, leaving Memorial Day week as our first available option. Plus, the weather is usually hit or miss on the East Coast that weekend, especially out east, and the water in May is still so cold. Same with Los Angeles, woah, June gloom is real. I thought you all lived there for the weather?!
Well, it turns out that late May is the perfect time to visit Hawaii. The weather was perfect, the ocean was so warm, and because school was still in session, tourists and the local crowds, especially on the weekdays, hadn’t quite started to accumulate. It was the perfect summer kick-off trip, and we’re even thinking about making this our annual trip.
So here is our list of places we enjoyed, along with our honest commentary, to help us remember and to help you plan your trip. I will mention that we haven’t traveled to other Hawaiian Islands, so I don’t know how this compares to Maui, Kauai, etc. But we kept hearing incredible things about those islands from locals, especially Kauai.
Accommodations:
Oahu is a 5-9 kind of place, meaning everyone is up and at it by sunrise at 5 am and in bed by 9 pm. Beaches and surf breaks are buzzing by 8 am, especially on the weekends, and most restaurants are trying to wrap things up by 9 pm. We were impressed by how active everyone was. The lifestyle suited us. We loved it.
Oahu is split into “Town” and “Country.” Town is Honolulu, and Country is the island's northern half, "the North Shore.” We recommend staying on the North Shore, in the Haleiwa area. The drive to Town will be an hour long (possibly longer during rush hour, which starts at 6 am), but there wasn’t one day that we weren’t up for the drive or so thankful for our evening on those beautiful North Shore beaches. If you’re there to surf, renting a house is the way to go. It was such a convenience to have a secure driveway to leave our boards on, a hose to rinse things off, a washer/dryer, etc. I would check AirBnb and VRBO for options. If you can’t find something suitable, contact me for a local property manager’s number. We also drove by Ke Iki Beach Bungalows a few times and it’s in a great location, and options look decent on the website!
Turtle Bay Resort, soon to be Ritz Carlton, is the only option if you want a hotel. It is definitely a full-on, White Lotus-style resort, but its recent renovation is impressive. It also has great boutiques, a sunset bar, and restaurant options, but more on that later.
If you want to stay in Town, the Kaimana Hotel is a cool boutique hotel. Most of the hotels in Honolulu-Waikiki will be enormous, mass-market resorts with an overload of cultural exploitation. Not for us! The Kaimana is about a half mile south of Waikiki, near the base of Diamond Head. What a difference that makes!! Book an ocean-facing room or suite. Not only will you be happy to wake up to that gorgeous view, but we heard all those rooms are nicely renovated and well-appointed. The hotel is exceptionally convenient if you are there to surf. There is a surf shop on the ground level and a few great breaks within view of the hotel, including Old Man’s/Sandbar, which is right in front.
Surf Shops & Boards
Oahu is ground zero for surfing. The whole time, we were comparing it to skiing in Utah. You know how, after landing in SLC, you can be on a mountain and skiing in a matter of hours? Oahu is the same. If you land at 11 am and HNL, you can be catching your first wave by 1 pm. If you are going in the summer, the South Shore will have the swell, and in the winter, the North Shore will have world-class surfing conditions and many pro surf contests.
Because of the time of year, we surfed in Town and stuck to Old Man’s/Sandbar, Queens, and Rockpile/Ala Moana Bowls. All had excellent longboarding conditions but a shallow reef bottom, so watch your feet! The other great thing about surfing in Oahu is that every break has a Surfline cam! So you can wake up and pick out a place to surf based on videos and who you see in the water. We didn’t find any of the breaks mentioned overly territorial or overly friendly. Waikiki is used to tourists, but it’s always good to be cautious and respectful your first few times out; you’ll see the same people every day.
We rented boards and reserved a guide through the Kai Sallas Longboard Co., located on the ground level of the Kaimana Hotel. Our guide, Noa, was so helpful on our first day out. The swell and winds were very challenging to read. Being on an island in the Pacific is not like Ditch Plains! If you have a specific board that you like to ride, I’m sure it’s easy to track down, but if you want a longboard designed for surfing the south shore, shaped by a WSL longboarding champion, Kai Sallas is the guy! A few friends from Montauk recommend his boards to us, including Adam Mar, who stocks them in his store. Also recommended for guides, lessons, and rentals were Ty Gurney’s Surf School and on the North Shore, the Jamie O’Brien Experience at Turtle Bay (great for beginners), or Uncle Bryan’s Surf School.
We also liked the North Shore Surf Shop in Haleiwa, and you must go to the Xcel store there. It’s Xcel’s only retail store, and it was fully stocked with different kinds of wetsuits, rash guards, and booties, all of which can be really hard to track down online, especially in the summer.
Places to Eat
The scene on the island is extremely casual—no need to pack anything fancy, not even a kitten heel. Anyone dressed up is so clearly on their honeymoon, so leave them alone! For us, it was a flip-flops all-day and all-night place. But just because everything is casual doesn’t mean average food or service. We were so impressed by the food and hospitality.
Chinatown is the most exciting part of Honolulu. You can tell from walking around that a revival of the area is in progress. I suggest spending some time there, it’s also the oldest part of the city, so the architecture is very interesting, too. Most of the restaurants below are in this area.
Pig and The Lady: This is the most hyped restaurant in Honolulu, and I’m happy to report that it met expectations. They’re famous for the Pho French dip sandwich, which you should order because it was excellent, but I thought the king salmon cà ri (curry) was way better. Start with the Burmese tea salad; that’s also a must.
Kyung’s Seafood: Our friend Winnie recommended this to us, and we regret not returning a second (or third) time. It's a very casual and local spot serving Korean-Hawaiian food. We had the best kalbi and poke of the trip here and the second best garlic shrimp.
O’Kim’s: Another Korean spot in Honolulu with a more traditional menu. If you are craving things like bibimbap or bulgogi, eat here. The truffle mandoo (dumplings) is a must!
Fête: Someone local recommended this, but we didn’t have the chance to visit. I believe it recently won a James Beard award. So, try it and let me know. I have it in mind for our next trip.
Duke’s Waikiki: If you’re going to eat anywhere in Waikiki, let it be Duke’s. It’s touristy but also a classic. It gets slammed, so be strategic when visiting or preparing to wait. We went at peak time on a Sunday, and even with how busy it was, our food and drinks came quickly and were delicious.
Sunset Provisions: A great little coffee shop and boutique at the Kaimana Hotel.
Hau Tree: Okay, maybe stay at the Kaimana Hotel because their restaurant, Hau Tree, was also fabulous. The outdoor area is set under massive Hau trees that provide shade to the whole area. We had the most nourishing post-surf brunch here. I loved my ahi poisson cru and the miso caesar salad.
Monsarrat Shave Ice: I am 50/50 on shave ice. It’s a lot of sugary, artificially colored, and flavored syrup to ingest. But I ended the trip by deciding that I liked it, but only at two places. Monsarrat is one of the two and the only place I came across serving all-natural purees on shave ice, not dayglo-colored syrup. It’s technically cash only, but they allowed me to pay via credit card at the connecting restaurant.
As casual as we found Honolulu to be, the North Shore is one notch more casual—not just in terms of dress but also by facility. Some of the best food in the area will come from food trucks and roadside shacks.
Sunrise Shack: There are multiple locations now (and franchise opportunities!), but I highly recommend going to the original location at Sunset Beach for breakfast or a post-surf snack. Everyone in Hawaii loves açai bowls, and the Sunrise Shack has great açai bowls and smoothies that also feel nutritious. Their coffee is solid, too!!
Coffee Gallery: This was our go-to afternoon caffeine hit spot. I started to crave their Da Kine latte every day around 2:30 pm. In addition to amazing drinks, they also have an extensive selection of Hawaiian coffee beans. We took a few bags home with us.
Aoki’s Shave Ice: Located across from the famous Matsumoto Shave Ice, which I found to be SO sweet and inedible. I loved Aoki’s flavors and toppings and found it all to be refreshingly sweet. They also serve a selection of ice creams, which were all really good, especially the ube and macadamia nut flavors. Ice cream is surprisingly hard to come by, shave ice is really everyone’s thing.
Pupukea Grill: This was our favorite food truck; we went multiple times for lunch. The chicken plate and wasabi ahi poke bowls are both outstanding and can easily be consumed on repeat. This is also a great place to spot the local pro surfers! They all eat here, and we noticed a few each time we visited.
The Beach House by Roy Yamaguchi: The “fine dining” option at Turtle Bay, another place we visited multiple times. If you were going to upgrade from regular flip-flops to leather flip-flops, this is the place to do it. The restaurant is right on the shore of Kulima Cove in an open-air, totally gorgeous setting. Reservations are required. Otherwise, the bar area is first come, first serve. With a few days’ notice, we had no problem getting a reservation and no issue getting seated in the bar area. The seared ahi tuna entree and the macadamia nut pie were the standouts for me!
Alaia: This is Turtle Bay’s farm-to-table option—a solid dinner option, especially if you couple it with sunset drinks at Sunset, at sunset.
Ranjanee Thai: This is where we had the best garlic shrimp of the trip. Their garlic shrimp is one of those dishes you want to compulsively eat until there’s nothing left, and consider ordering a second not because you're hungry but because you don’t want the flavors to leave you. The drunken noodles were spot on as well.
Banzai Sushi Bar: Another North Shore hit! There is a big section of tatami seating on the porch, so dress accordingly. The staff was so friendly and very efficient. The whole place had such a great vibe to it. The menu offers a large selection of sushi bar classics. We ordered a bunch of nigiri and poke to start, which tasted fresh and flavorful. (Side note: I’ve noticed on several occasions now that nigiri on the West Coast tends to be bigger/longer cuts than on the East Coast or in Japan. Is this a thing?).
Lei Lei’s: Located at the Golf Course at Turtle Bay, but is run independently from the rest of the hotel. We didn’t have the chance to go on this trip, but I visited here several years ago and remember it fondly. All of the pro surfers like eating here, too!
Places to Shop
Number808: Probably the best boutique on the North Shore. Great selection of surf brands, vintage T-shirts, antiques, and well-designed store merch. Matt and I both found a few things we loved here.
Single Double: A well-curated vintage boutique in Chinatown (Honolulu). They have an interesting mix of vintage clothing and accessories for both men and women, priced reasonably. One of the owners also owns and designs Hula Eyewear, a brand to keep tabs on. I have two pairs that I love!
Baileys Antiques & Aloha Shirts: Aloha overload. This place is literally stuffed to the gills with vintage Hawaiian aloha shirts and antiques. Be prepared for an overwhelming experience!! Browse all the racks, but the best stuff is all hanging from the ceiling and is the most expensive.
SantoLoco Surf and Skate: We wanted to go in here so badly, but we never passed by it during their opening hours. Someone, please check it out for us!
On Land
Outrigger Canoe Club: The Outrigger was the best vacation upgrade ever received. It’s like the New York Athletic Club of Oahu but with a huge emphasis on all water sports and, as the name would suggest, outrigger canoeing. One of Matt’s colleagues is a member here and called in a guest pass for us. Not only were the guest passes very reasonable ($120 for the two of us for a week), but it granted us full access to the club and its services, including direct ocean access via the private beach access (although it was closed most days while we were there because a monk seal and her pup were bonding on the beach). It has a great restaurant, snack bar, lockers to rent, sauna, showers, parking, and beach volleyball. It was the best amenity to have access to, especially if you’re not staying in Honolulu.
If you don’t know anyone in Honolulu but you are a member of any Ivy University clubs or NYAC/Jonathan Club-type clubs in the US, check for reciprocity. Our experience made us want to join one of those clubs rather than all these new ones popping up in NYC and LA. Having reciprocity with a worldwide network of Clubs like the OCC is a huge perk!
Hiking is also great on the North Shore. We did the Kaunala Trail and the Lanikai Pillbox Trail. The Kaunala Trail will take a few hours, and the Pillbox Trail is a very quick out-and-back and has a great Western view of the ocean. Go just before sunset to enjoy it!