Though the majority of Oahu’s population calls Honolulu home, there’s much more beyond Hawaii’s capital city. Of course, the ideal 48-hour stay calls for time spent in both the metropolis (or as much of a metropolis a city can be on a Pacific island) and on the remote North Shore. After a recent trip exploring all Oahu has to offer, our Forbes Travel Guide editors have curated a jam-packed, two-day itinerary, ensuring your vacation will be as perfect as the weather.
Day One
Your home for the first 24 hours will be Trump International Hotel Waikiki Beach Walk. The sprawling rooms and suites feel more like luxurious condos than hotel rooms, thanks to amenities such as gourmet kitchens with Sub-Zero and Wolf appliances, and spacious marble bathrooms. Though it’s not perched right on the sand, the glamorous resort is just on the other side of the block from the Pacific Ocean and offers beach service (and supplies you with beach bags stocked with towels, bottled water, fruit and sunscreen). If you don’t feel like sinking your toes in the sand, you can head up to the sixth-floor infinity pool and sip handcrafted cocktails (we suggest a Mai Tai).
If you want a dose of history, book a room at Moana Surfrider, A Westin Resort & Spa. Nicknamed the “First Lady of Waikiki,” it’s the original Waikiki resort. The colonial-esque hotel stands guard over the beach, with its iconic banyan tree as the centerpiece. One of the perks about staying here is that you have access to the other Starwood properties in Waikiki (including The Royal Hawaiian) and can even charge things back to your room. That means, if you want to get a surf lesson at the luxurious pink hotel (see next paragraph) and don’t want to bring your wallet, you can just add it to your bill.
Considering you’re staying in Waikiki, some time on the beach is definitely in order. Start your day with surf lessons—this is where surfing was popularized, after all. Even if you haven’t caught a wave in your life, this is the place to learn. The waves in Waikiki are typically beginner friendly, though if you venture to the beach around sunrise, you’ll spot plenty of veteran surfers. Venture from your hotel over to The Royal Hawaiian (it’s the massive pink resort, you can’t miss it), where you’ll find Waikiki Beach Services and its crew of stellar surfers. When we were there, we paddled out with Pohai McWhirter, who was more than patient (even after a few spills on our part).
After your surf lesson, you’ll be ready for a bite to eat before continuing on your Honolulu adventure. For a quintessential meal, make your way toward Diamond Head (the site of your next activity) and stop at Diamond Head Cove Health Bar. It’s a tiny spot in a strip mall that only accepts cash, but once you bite into that açai bowl, you’ll forget about the nondescript location. We suggest ordering Da Cove Bowl, which is a large scoop of puréed açai berries (frozen, so it has the consistency of a smoothie) that’s topped with honey, granola, bananas and strawberries. It’s technically the smallest size, but trust us when we say it’s big enough for two.
Once you’ve fueled up, it’s time to do one of the more touristy—yet completely worth it—things in Honolulu: hike up Diamond Head. Getting to the summit of the volcanic crater will take about an hour; you’ll climb on a switchback, head up a series of stairs and tunnels before reaching a World War II bunker. Once you’ve reached the top, you’ll be rewarded with stunning views (some of the best on the island, in fact).
Now that you’ve got two activities under your belt for the day, you can soak up the sun on the beach or by the pool. This is the perfect time to refuel with some fish tacos or ahi poke, which will likely be some of the freshest fish you’ve tasted. Be sure to put on sunscreen and drink plenty of water because you still have about 36 hours to go in your Oahu vacation.
Rinse off the salt and sand, and get to Honolulu’s Chinatown for a tour of the city, courtesy of Holoholo Bicycles. Brandon Reid, who co-owns the shop with his wife, Nicole, will fit the stylish beach cruiser to your liking and guide you through historic Honolulu. On your 90-minute ride, you’ll stop at landmarks such as the ‘Iolani Palace, the Hawaii State Capitol building and Aloha Tower.
Oahu is all about being active, and you’ve gotten your fair share today. Head back to your hotel to freshen up before dinner. Your day isn’t over just yet. Foodies will want to make a beeline for Vintage Cave, which, oddly enough, sits inside the Japanese department store Shirokiya inside Ala Moana Center. Don’t let its location fool you though, this dynamic restaurant offers just one tasting menu—at $295 per person—and just one seating per night. Chef Chris Kajioka does wonders with his ingredients. Prepare to savor dishes such as local sashimi and Shinsato suckling pig.
For those looking for a more casual dinner, indulge in ramen—one of the hottest dishes in the culinary world these days. We suggest heading to Hokkaido Ramen Santouka, the city’s newest ramen shop; just be ready for an hourlong wait.
Day Two
It’s time for you to see another part of this paradise. Your second day will be spent on Oahu’s famous North Shore. There’s no rush to get out there, but you’ll probably want to get a head start on the hourlong drive. Set out on your scenic journey in mid-morning, allowing you to make a delicious pit stop just before you arrive at Turtle Bay Resort—your residence for the second part of your trip. For the best views (and food) along the way, you’ll want to take the coastal route. About five minutes before you arrive at the resort, you’ll spot shrimp trucks on the right side of the road in Kahuku. This is lunch (or perhaps a late-morning snack). They all essentially serve the same thing, so it’s a matter of which truck has the shortest line. We stopped at Fumi’s Kahuku Shrimp and ordered the garlic shrimp plate, which comes with a handful of tasty shrimp, two scoops of rice and a small salad. It really hits the spot.
After you’ve chowed down, continue on Kamehameha Highway until you spot the Turtle Bay resort on the left-hand side. The massive, 840-acre resort has just about everything you could want in a property, including stables, golf courses, restaurants and even helicopter tours. Check into your room—all of the rooms and suites in the main building are freshly renovated—and change into your bathing suit because it’s time for a stand-up paddleboard lesson.
Located just off the lobby, Hans Hedemann Surf School offers a variety of water activities. But if you’re here in the winter and have never surfed before, we suggest sticking to stand-up paddling. It’s a great workout for the core, so you’ll feel like you’ve really earned a treat after the hour lesson. If you need a bit of rest and you are here during the colder months, grab a chair by the pool and position it to face the ocean, allowing you to watch expert surfers catch some massive waves.
The North Shore is a rather idyllic place. It feels worlds away from the high-rises of Honolulu, and perhaps one of the most picture-perfect spots is the surf town of Haleiwa, which sits about 15 minutes north of Turtle Bay. Venture into town for yet another must-try Hawaiian specialty: shave ice. We suggest going to Matsumoto Shave Ice. The line is almost always out the door, but it’s definitely worth it. The finely-shaved ice is topped with whichever flavor you choose (or combination) and you can add on ice cream, sweet azuki beans and condensed milk.
Explore Haleiwa a bit; check out the Clark Little Gallery, where you’ll find gorgeous photographs of the ocean. Little actually shoots these stellar images in the water, offering a unique perspective (think inside the pipe of a wave with the sunset in the background).
Make your way back to Turtle Bay after you’ve soaked up all that Haleiwa has to offer. If you’re a thrill-seeker, we suggest booking a helicopter tour in the resort’s Magnum P.I. chopper. To really get your adrenaline pumping, request to fly with the doors off. Embark on a 20-minute tour, during which you’ll spot the biggest surf spots (Sunset Beach, Banzai Pipeline and Waimea Bay), Waimea Valley and Sacred Falls.
With your heart pounding, head back to your room to relax on the balcony before getting ready for the evening. Since there isn’t much else on the North Shore (that’s the beauty of it), dinner will be at Turtle Bay. The good news is that there are plenty of restaurants to choose from, including beachfront Ola, which you may recognize from the movie Forgetting Sarah Marshall. The menu is highlighted by local ingredients; and when you’re sitting right on the beach, it doesn’t get much more Hawaiian than that. Start with some ahi poke that’s made with local ahi tuna, North Shore limu (Hawaiian for algae), arugula from Pupukea and Kahuku sea asparagus. It’s light and fresh—a great way to begin your meal. As for your main course, we suggest going with one of the fresh fish dishes, so you can make the most of your Oahu vacation.
Finish off your two-days on Oahu with a cocktail at Surfer, The Bar. Sitting just off the lobby, the lively bar hosts all kinds of events, ranging from karaoke to “Talk Story,” which is held every Wednesday night and features surfing legends sharing their tales.
Photos Courtesy of Hawaii Tourism Authority-Tor Johnson, Oahu Visitors Bureau and Turtle Bay Resort
