The Secret to a Perfect Oahu Vacation
I spent most of my childhood on Oahu’s North Shore, on a five-acre farm right on the beach—just five miles from the quaint surfing town of Haleiwa and another five from the biggest surfing beaches in the world: Pipeline, Sunset Beach, Waimea Bay. The town is quaint and energetic, with a real sense of community, or what us locals call “ohana.”
It’s been well over 25 years since I left my hometown, but I’ve been back at least once every year. My family has grown. My tastes have changed. (I’m a true New Yorker at this point.) Yet I always come back to the same hidden spots, and every time, I'm reminded that Oahu doesn't deserve its Waikiki tourist trap reputation. If navigated right, it can offer the best of both worlds: down-to-earth local activities and elevated luxury experiences. It all starts on Oahu’s North Shore. Here are my secrets.
Over the last three decades, I have stayed at pretty much every five-star resort across the island chain. But if you want the convenience of traveling without a connecting flight, and truly untouched, raw natural beauty, I recommend The Ritz Carlton Turtle Bay Resort on Oahu’s North Shore. I’ve stayed at this hotel maybe a dozen times, but in 2020 it underwent a massive, multi-year renovation that elevated the property to an impressive new level.
Just this past year it was acquired by The Ritz, which should give you a sense of the hospitality standards and experience you can now expect. Most recently, my family and I stayed at their Ocean Suites, which are only an eight-minute walk from the main hotel. (Still, if you’re not looking to get your extra steps in while vacationing, the resort provides golf carts that can shuttle you anywhere.) Situated on a secluded beach, the suites have a private pool and personal bartender. Venture beyond your private villa, and you’ll find a sprawling 1,300 acres—complete with beachfront horseback riding, a sweet little surfing spot, and a beautiful 20-acre sustainable farm that provides fresh produce for the hotel and local community. Plus, there are three pools—one equipped with two water slides—so your little ones can join in on the fun. (Can you tell I have two toddlers?)
What I love about Turtle Bay is the synchrony of local community and luxury. You can’t see a single other resort nearby—because there aren’t any. Only 15 minutes away from everything North Shore has to offer, the hotel calls upon local artisans and craft makers across every element of the experience, creating a truly authentic, immersive experience. As a local Hawaiian, I can honestly say that I feel at home.
Pro tip: If you get an Ocean room, you’ll have access to The Club, which has all-day on-demand dining, happy hour, and some of the best views at the resort. In my view, this is a must-have for families.
Beach hop from Waimea Bay to Banzai Pipeline Beach to Sunset Beach. If you’re feeling adventurous, I suggest starting your day at 8:00am—traffic can get bad in the winter months, especially during the big surf contests. You’ll want to visit Waimea Bay early in the morning to beat out the crowd. If you’re traveling during the winter surf season, you might get lucky and catch the Eddie Aikau Big Wave Invitational, the world-renowned surfing competition that only happens when there are 40-foot waves. If you’re visiting in summer months, consider testing your bravery and jumping off the Big Rock at Waimea. It’s an exhilarating experience!
Stumble upon Lanikakea beach, nicknamed Turtle Beach. As you’re driving along Farrington Highway, the only road around the North Shore, you’ll eventually hit this area and can park off the road. Hop off and you’ll often see dozens of turtles sunbathing and relaxing on the sand. (I’ve seen up to 30 turtles at once there!) Pro tip: If you walk around the bend of this beach, you’ll see another stunning, sprawling beach that is far more secluded than any of the main surfing spots.
Discover Turtle Bay’s secret beach, Kawela Bay, one of the most secluded beaches on Oahu. The waters are calm year-round, and the sandy beach is backed by beautiful ironwood trees and coconut palms. It feels like a jungle-meets-beach experience. Pro tip: Grab a free bike on the Turtle Bay Resort property and ride along the bike paths to the beach.
Take a stroll through Waimea Valley, a hidden oasis with 1,875 acres of botanical gardens leading up to a beautiful waterfall. This recommendation can be a bit polarizing as the gardens are paved and can feel touristy, but I would still put it on the list if you want to see hundreds of tropical flowers. It’s an easy destination that the entire family can enjoy. It’s also steps away from Waimea Bay so you can hit up both spots in a single afternoon. There’s a better-than-decent food court, and if your trip is timed right, you might be able to catch one of the famous Moon Walks.
Check out Kualoa Ranch. While Kualoa is one of the most hyped-destinations on Oahu, it’s worth visiting if you’re already staying out on the North Shore. It was the filming location for dozens of movies from Jurassic Park to 50 First Dates—and the mountains across the valley are some of the most striking views you’ll see. I recommend the UTV Raptor Tour, where you’ll get a two-hour private tour on a buggy that will take you into the depths of the jungle and valley.
Take a surfing lesson with the Jamie O’Brien Surf Experience, North Shore’s premier surf school. You can sign up for lessons and rent boards on the Ritz Carlton Turtle Bay property, and there's a quaint surf break right in front of the hotel. You’ll find local kids surfing the break as well as beginner adults—it's the perfect surf spot all year round.
While you won’t get Michelin-level restaurants on the North Shore, there are some great casual dining options that consistently deliver the depth and complexity of Hawaiian flavors that locals love, from tropical fruits like pineapple, lilikoi (passionfruit), mango, and taro to quintessential dishes like kalua pork, chicken laulau, and loco moco.
Roy’s Beach House: Located on the Turtle Bay property, Roy’s is one of the more upscale restaurants and is known as the creator of Hawaiian-fusion cuisine.
Beach House: Closer to Haleiwa, Beach House has delicious cocktails and one of the best loco mocos on the island.
Farm To Barn: This is hands-down my favorite spot on the North Shore—super casual with picnic table seating and a live Hawaiian band on Saturday mornings. I highly recommend their Buddha Bowl and Hapa Bowl (an inspired take on a traditional Acai bowl.)
Island Vintage Coffee: A Hawaii staple, this spot is known for its Macadamia Kona Mocha (you won’t regret it.)
Sunset Beach Food Trucks: There is a lot of debate around the shrimp trucks on the North Shore. Giovanni’s is the original location, and is delicious, but you’ll have to deal with long lines and uncomfortable picnic tables. If you head over to the opposite end of the North Shore at the Sunset Beach Food Trucks, you’ll find the same quality, but a more relaxing experience and shorter lines.
Kulima Farms: Stop by the food stands outside this 468-farm that powers the Ritz Carlton Turtle Bay Resort. You can pick up some local fruits and Hawaiian treats, all home grown on the North shore.
Celestial Natural Foods: A local favorite, Celestial Natural Foods is a quaint little grocery store with organic goodies from local farmers and businesses. It’s been around since 1974, and it's a great spot to stock up on snacks for the trip. Be sure to grab ingredients for tacos with Raiz Tortillas, locally-produced, small-batch heirloom tortillas, developed by my dear friends Kim Shibata and Ray German. Their corn is sustainably sourced from small rural farms in Mexico, and made by hand on Oahu to create a tortilla that is fragrant, rich and flavorful. (I promise, you will notice the difference!)
Matsumoto’s Shave Ice: This is by far the most touristy spot on the North Shore, but it’s one of those places that you just have to try. It’s home to the most famous Shave Ice on the island and is a staple. Is it overrated? Maybe. But the lines go fast, it’s iconic—I’d argue that it’s a historic landmark for islanders—and it’s worth checking off the list.
The Growing Keiki: The best spot for local children’s gifts, Growing Keiki is a small, magical shop at the end of the Haleiwa strip. You’ll find everything here, but be sure to snag some gifts from Keiki Kaukau, a brand created by my best childhood friend, April Hail. You’ll find a vast selection of beautifully crafted toys, Montessori activities, and books that reflect the rich culture and diversity of the Aloha State.
Breeze at the Turtle Bay resort: I stumbled upon this tiny luxury boutique in the Turtle Bay Resort and was taken aback by the merchandise assortment. They had incredible vintage Chanel bags sourced from Fred Segal in LA—something you can’t find anywhere else in Oahu.
Guava Shop: Shop upscale bags, swimsuits, and beachwear ranging from local artisan labels to global brands like Ulla Johnson.
No. 808: In my opinion, this store offers best vintage Hawaiian goods you can find on the island. Expertly curated with an elevated design aesthetic, Number 808 carries an eclectic mix of old and new Hawaiian labels.
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